GB877039A - Manufacture of halogen-substituted isoindolinones - Google Patents
Manufacture of halogen-substituted isoindolinonesInfo
- Publication number
- GB877039A GB877039A GB39660/58A GB3966058A GB877039A GB 877039 A GB877039 A GB 877039A GB 39660/58 A GB39660/58 A GB 39660/58A GB 3966058 A GB3966058 A GB 3966058A GB 877039 A GB877039 A GB 877039A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isoindoline
- substituted
- nitro
- alkyl
- diamino
- 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
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001555 benzenes Chemical class 0.000 abstract 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical class OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- CUVAUYUUVFGQAI-UHFFFAOYSA-N 3,3,4,5,6,7-hexachloro-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)NC(Cl)(Cl)C2=C1Cl CUVAUYUUVFGQAI-UHFFFAOYSA-N 0.000 abstract 1
- UMCMKIAEDPXIIC-UHFFFAOYSA-N 3,3,4,7-tetrachloro-2H-isoindol-1-one Chemical compound ClC1(NC(C2=C(C=CC(=C12)Cl)Cl)=O)Cl UMCMKIAEDPXIIC-UHFFFAOYSA-N 0.000 abstract 1
- VAHDGGHQFWBIEQ-UHFFFAOYSA-N 3,3-dichloro-6-methylsulfonyl-2H-isoindol-1-one Chemical compound CS(=O)(=O)C1=CC=C2C(NC(C2=C1)=O)(Cl)Cl VAHDGGHQFWBIEQ-UHFFFAOYSA-N 0.000 abstract 1
- FGVHEXQSFQLKCA-UHFFFAOYSA-N 3,3-dichloro-6-nitro-2H-isoindol-1-one Chemical compound [N+](=O)([O-])C1=CC=C2C(NC(C2=C1)=O)(Cl)Cl FGVHEXQSFQLKCA-UHFFFAOYSA-N 0.000 abstract 1
- MMBYJYAFFGKUDC-UHFFFAOYSA-N 3-aminoisoindol-1-one Chemical class C1=CC=C2C(N)=NC(=O)C2=C1 MMBYJYAFFGKUDC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000004760 aramid Substances 0.000 abstract 1
- 229920003235 aromatic polyamide Polymers 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
3,3-Dihalo-isoindolin-1-ones of the formula <FORM:0877039/IV (b)/1> where the benzene nucleus can be substituted are prepared by reacting a 1,3,3-trihalo-isoindolenine at below 100 DEG C., advantageously in an inert organic solvent, with the equimolar amount of a compound ROH, where R is hydrogen, alkyl (which may be substituted), aralkyl or cycloalkyl or an aliphatic or aromatic carbacyl radical. Specified substituents in the benzene nucleus are nitro, trifluoromethyl, alkyl or aryl sulphonyl, and particularly several halogen atoms, such as F, Cl and Br, e.g. three and four chlorine atoms. Specified compounds ROH are water, methanol, ethanol, butanol, octanol, benzyl alcohol, cyclohexanol, ethylene glycol, methoxyethanol, ethoxyethanol, and acetic, propionic, chloracetic, benzoic and chlorobenzoic acids. The products of the invention are of use in the manufacture of azomethine dyestuffs (see Group IV(c)). Specification 833,548 is referred to. Reference has been directed by the Comptroller to Specification 704,595.ALSO:Azomethine dyestuffs are prepared by the reaction of aromatic polyamides with 3, 3-dihalo-isoindoline-1-one of formula:- <FORM:0877039/IV(c)/1> (where the benzene nucleus may be substituted, e.g. by nitro, trifluoromethyl, alkyl or aryl sulphonyl, or several halogen atoms), either directly or after reaction of the isoindolinones with ammonia or primary organic amines to form the corresponding 3-imino-isoindoline-1-ones. Examples refer to the reaction of benzidine with 3, 3, 4, 5, 6, 7-hexachloro-isoindoline-1-one; of 1, 4-diamino benzene or 4, 41-diaminodiphenyl with 3, 3, 4, 7-tetrachloro-isoindoline-1-one; of 4, 41-diamino-3, 31-dimethyldiphenyl with 5- or 6-nitro-3, 3-dichloro-isoindoline-1-one; and of 4, 41-diaminodiphenyl and 4, 41-diamino-3, 31-dimethoxydiphenyl with 5- or 6-methylsulphonyl-3, 3-dichloroisoindoline-1-one. Specification 833,548 is referred to. Reference has been directed by the Comptroller to Specification 704,595.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH877039X | 1957-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB877039A true GB877039A (en) | 1961-09-13 |
Family
ID=4544492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39660/58A Expired GB877039A (en) | 1957-12-10 | 1958-12-09 | Manufacture of halogen-substituted isoindolinones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB877039A (en) |
-
1958
- 1958-12-09 GB GB39660/58A patent/GB877039A/en not_active Expired
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