Ethanol → N-(4-amino-2-methylphenyl)-2-chloroacetamide
Reaction equation
S1C=CC=C1.C(O)C.[Cl:9][CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=1[CH3:23])=[O:12].[H][H]>[Pt].CO>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[CH2:10][Cl:9])=[C:15]([CH3:23])[CH:16]=1Participants
Procedure
To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol were added 15 parts of 2-chloro-N-(2-methyl-4-nitrophenyl)acetamide and 400 parts of methanol. The whole was hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The solid residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 12 parts (92%)of N-(4-amino-2-methylphenyl)-2-chloroacetamide (intermediate 70).
Workup
- filtrationthe catalyst was filtered off
- customthe filtrate was evaporated
- customThe solid residue was purified by column-chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
- customThe pure fractions were collected
- customthe eluent was evaporated
- filtrationThe product was filtered off
- customdried
Sources & evidence
- ORD record
- ord-9a978e6b54644696a6d3ec32141b02be
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04766125
Reaction notes
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