AU2001260124A1 - Method for producing n-butyryl-4-amino-3-methyl-methyl benzoate and the novel compound n-(4-bromine-2-methylphenyl)-butanamide - Google Patents
Method for producing n-butyryl-4-amino-3-methyl-methyl benzoate and the novel compound n-(4-bromine-2-methylphenyl)-butanamideInfo
- Publication number
- AU2001260124A1 AU2001260124A1 AU2001260124A AU6012401A AU2001260124A1 AU 2001260124 A1 AU2001260124 A1 AU 2001260124A1 AU 2001260124 A AU2001260124 A AU 2001260124A AU 6012401 A AU6012401 A AU 6012401A AU 2001260124 A1 AU2001260124 A1 AU 2001260124A1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- butanamide
- butyryl
- methylphenyl
- bromine
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 229940095102 methyl benzoate Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
According to the invention, N-butyryl-4-amino-3-methyl-methyl benzoate is obtained in a particularly advantageous manner by, initially, reacting o-toluidine with butyric acid chloride, by brominating the reaction product and by reacting the bromide obtained therefrom with carbon monoxide and methanol in the presence of a palladium catalyst. The invention also relates to the important novel chemical compound N-(4-bromine-2-methylphenyl)-butanamide.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10015279 | 2000-03-28 | ||
DE10015279A DE10015279A1 (en) | 2000-03-28 | 2000-03-28 | Process for the preparation of N-butyryl-4-amino-3-methyl-benzoic acid methyl ester and the new compound N- (4-bromo-2-methylphenyl) butanamide |
PCT/EP2001/002924 WO2001072690A2 (en) | 2000-03-28 | 2001-03-15 | Method for producing n-butyryl-4-amino-3-methyl-methyl benzoate and the novel compound n-(4-bromine-2-methylphenyl)-butanamide |
Publications (1)
Publication Number | Publication Date |
---|---|
AU2001260124A1 true AU2001260124A1 (en) | 2001-10-08 |
Family
ID=7636623
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2001260124A Abandoned AU2001260124A1 (en) | 2000-03-28 | 2001-03-15 | Method for producing n-butyryl-4-amino-3-methyl-methyl benzoate and the novel compound n-(4-bromine-2-methylphenyl)-butanamide |
Country Status (9)
Country | Link |
---|---|
US (2) | US6620962B2 (en) |
EP (1) | EP1268400B1 (en) |
JP (1) | JP2003528846A (en) |
CN (1) | CN1184194C (en) |
AT (1) | ATE273270T1 (en) |
AU (1) | AU2001260124A1 (en) |
DE (2) | DE10015279A1 (en) |
ES (1) | ES2227193T3 (en) |
WO (1) | WO2001072690A2 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5001187A (en) * | 1989-10-16 | 1991-03-19 | Dow Corning Corporation | Emulsions of silicone elastomer |
WO2004009051A2 (en) * | 2002-07-18 | 2004-01-29 | Quest International Services B.V. | Perfume compositions |
JP2007525274A (en) * | 2004-02-27 | 2007-09-06 | ロジャー・ピー・ジャクソン | Orthopedic implant rod reduction instrument set and method |
KR20230110301A (en) * | 2020-11-18 | 2023-07-21 | 디에스엠 아이피 어셋츠 비.브이. | Novel synthesis of L-phenylalanine butyramide |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW397819B (en) * | 1994-03-31 | 2000-07-11 | Nihon Nohyaku Co Ltd | A process for producing a substituted benzoyl fatty acid derivative |
-
2000
- 2000-03-28 DE DE10015279A patent/DE10015279A1/en not_active Withdrawn
-
2001
- 2001-03-15 CN CNB018072046A patent/CN1184194C/en not_active Expired - Fee Related
- 2001-03-15 JP JP2001570605A patent/JP2003528846A/en active Pending
- 2001-03-15 ES ES01933703T patent/ES2227193T3/en not_active Expired - Lifetime
- 2001-03-15 US US10/239,678 patent/US6620962B2/en not_active Expired - Fee Related
- 2001-03-15 DE DE50103229T patent/DE50103229D1/en not_active Expired - Lifetime
- 2001-03-15 AT AT01933703T patent/ATE273270T1/en active
- 2001-03-15 WO PCT/EP2001/002924 patent/WO2001072690A2/en active IP Right Grant
- 2001-03-15 EP EP01933703A patent/EP1268400B1/en not_active Expired - Lifetime
- 2001-03-15 AU AU2001260124A patent/AU2001260124A1/en not_active Abandoned
-
2003
- 2003-08-04 US US10/633,863 patent/US20040030183A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
DE50103229D1 (en) | 2004-09-16 |
US20040030183A1 (en) | 2004-02-12 |
ATE273270T1 (en) | 2004-08-15 |
US20030065211A1 (en) | 2003-04-03 |
WO2001072690A2 (en) | 2001-10-04 |
CN1419535A (en) | 2003-05-21 |
EP1268400B1 (en) | 2004-08-11 |
CN1184194C (en) | 2005-01-12 |
EP1268400A2 (en) | 2003-01-02 |
JP2003528846A (en) | 2003-09-30 |
ES2227193T3 (en) | 2005-04-01 |
DE10015279A1 (en) | 2001-10-04 |
WO2001072690A3 (en) | 2002-02-28 |
US6620962B2 (en) | 2003-09-16 |
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