GB618034A - Manufacture of basically substituted 9:10-dihydroanthracene derivatives, and their salts and amino-oxides - Google Patents
Manufacture of basically substituted 9:10-dihydroanthracene derivatives, and their salts and amino-oxidesInfo
- Publication number
- GB618034A GB618034A GB3075746A GB3075746A GB618034A GB 618034 A GB618034 A GB 618034A GB 3075746 A GB3075746 A GB 3075746A GB 3075746 A GB3075746 A GB 3075746A GB 618034 A GB618034 A GB 618034A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dihydroanthracene
- amino
- acids
- salts
- dihydroanthracenes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- BDCIZVMGTWOOIY-UHFFFAOYSA-N 1,10-dihydroanthracene Chemical class C1=CC=C2C=C3CC=CC=C3CC2=C1 BDCIZVMGTWOOIY-UHFFFAOYSA-N 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 4
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 150000001340 alkali metals Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 monosodium compound Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 150000001243 acetic acids Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000004946 alkenylalkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 150000004680 hydrogen peroxides Chemical class 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Basically substituted 9 : 10-dihydroanthracenes of the general formula <FORM:0618034/IV(b)/1> wherein R represents a bivalent aliphatic radical and Am is the residue of a secondary amine, are prepared by reacting in equimolecular proportions an ester of an alcohol of the general formula HO-R-Am, wherein R and Am have the above significance, such as a hydrohalic acid ester or arylsulphonic acid ester with a compound of the general formula <FORM:0618034/IV(b)/2> wherein A1 represents an alkali metal and A2 represents hydrogen or an alkali metal, and when A2 represents an alkali metal, the reaction product is decomposed with water, alcohol or like compound containing reactive hydrogen. The monosodium compound of 9 : 10-dihydroanthracene may be prepared by reacting equimolecular proportions of 9 : 10-dihydroanthracene and sodamide and the product may then be reacted with a dimethylaminoalkyl halide. The basically substituted 9 : 10- dihydroanthracenes may be converted into salts by the addition of inorganic or organic acids, into quaternary ammonium salts by the addition of esters of aliphatic or araliphatic alcohols, e.g. alkyl-, alkenyl- and aralkyl halides, alkylene dihalides, dialkyl sulphates or arylsulphonic-acid esters, or may be converted into amino-oxides by means of oxidizing agents, e.g. hydrogen peroxides or per-acids. In examples, the following compounds are prepared: 9-b -dimethylaminoethyl-9 : 10-dihydroanthracene, its hydrochloride salt, the quaternary salts formed by the addition of ethyl bromide or methyl iodide and its amino-oxide, 9 - b - diethylaminoethyl-, 9 - b - (N - methyl - N - isopropylamino) - ethyl-, 9 - b - piperidinoethyl-, 9 - b - morpholinoethyl-, 9-g -diethylaminopropyl-and 9 - b - dimethylaminopropyl - 9 : 10 - dihydroanthracenes and their hydrochlorides. Other acids which may be used for salt formation are hydrobromic, sulphuric, phosphoric and acetic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3075746A GB618034A (en) | 1946-10-16 | 1946-10-16 | Manufacture of basically substituted 9:10-dihydroanthracene derivatives, and their salts and amino-oxides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3075746A GB618034A (en) | 1946-10-16 | 1946-10-16 | Manufacture of basically substituted 9:10-dihydroanthracene derivatives, and their salts and amino-oxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB618034A true GB618034A (en) | 1949-02-15 |
Family
ID=10312661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3075746A Expired GB618034A (en) | 1946-10-16 | 1946-10-16 | Manufacture of basically substituted 9:10-dihydroanthracene derivatives, and their salts and amino-oxides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB618034A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676971A (en) * | 1951-04-21 | 1954-04-27 | Searle & Co | Quaternary ammonium derivatives of aminoalkylxanthenes and aminoalkylthiaxanthenes |
| US2783237A (en) * | 1953-10-12 | 1957-02-26 | Irwin Neisler And Company | Bis-dialkylaminoalkylene bis-polycyclic ammonium salts |
| DE1177633B (en) * | 1961-02-17 | 1964-09-10 | Kefalas As | Process for the preparation of aminoalkylated 9,10-dihydroanthracenes |
| US3271451A (en) * | 1962-07-03 | 1966-09-06 | Merck & Co Inc | Process for preparing 5-(3-methylaminopropyl)-5h-dibenzo [a, d] cycloheptenes |
| US3299139A (en) * | 1963-02-20 | 1967-01-17 | Dumex Ltd As | 5-(3'-dimethylaminopropylidene)-dibenzo [a, d]-cyclohepta-[1, 4]-diene nu-oxide and hydrochloride thereof |
| US3409640A (en) * | 1959-07-22 | 1968-11-05 | Schering Corp | 5-(3'-dimethylamino-2'-methyl-propyl)dibenzocycloheptenes |
| US3513201A (en) * | 1966-10-25 | 1970-05-19 | Merck & Co Inc | Process for preparing 5-(3-alkylaminopropyl)-5h-dibenzo(a,d)cycloheptenes |
| US4153629A (en) * | 1975-12-15 | 1979-05-08 | Shionogi & Co., Ltd. | 9,10-Dihydro-9,10-methanoanthracene N-oxide |
-
1946
- 1946-10-16 GB GB3075746A patent/GB618034A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676971A (en) * | 1951-04-21 | 1954-04-27 | Searle & Co | Quaternary ammonium derivatives of aminoalkylxanthenes and aminoalkylthiaxanthenes |
| US2783237A (en) * | 1953-10-12 | 1957-02-26 | Irwin Neisler And Company | Bis-dialkylaminoalkylene bis-polycyclic ammonium salts |
| US3409640A (en) * | 1959-07-22 | 1968-11-05 | Schering Corp | 5-(3'-dimethylamino-2'-methyl-propyl)dibenzocycloheptenes |
| DE1177633B (en) * | 1961-02-17 | 1964-09-10 | Kefalas As | Process for the preparation of aminoalkylated 9,10-dihydroanthracenes |
| US3271451A (en) * | 1962-07-03 | 1966-09-06 | Merck & Co Inc | Process for preparing 5-(3-methylaminopropyl)-5h-dibenzo [a, d] cycloheptenes |
| US3299139A (en) * | 1963-02-20 | 1967-01-17 | Dumex Ltd As | 5-(3'-dimethylaminopropylidene)-dibenzo [a, d]-cyclohepta-[1, 4]-diene nu-oxide and hydrochloride thereof |
| US3513201A (en) * | 1966-10-25 | 1970-05-19 | Merck & Co Inc | Process for preparing 5-(3-alkylaminopropyl)-5h-dibenzo(a,d)cycloheptenes |
| US4153629A (en) * | 1975-12-15 | 1979-05-08 | Shionogi & Co., Ltd. | 9,10-Dihydro-9,10-methanoanthracene N-oxide |
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