Reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:4]=1[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:6].[H][H]>[Pd].C(OCC)(=O)C>[NH2:23][C:20]1[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[C:4]([CH:19]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:13][CH:14]=1)=[O:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To 26.6 g of 2-methoxy-5-nitro-N-(4-trifluoromethylbenzyl)benzamide were added 270 ml of ethyl acetate and 2.6 g of 10% palladium on carbon under an atmosphere of argon, then argon was replaced with hydrogen gas, and the mixture was stirred for 8 hours at room temperature under an atmosphere of hydrogen gas. Catalyst was filtered through Celite(Hyflo Super-cel) and, after washed the collected material well with ethyl acetate, the filtrate was concentrated under reduced pressure. The residue obtained was purified by means of column chromatography (silica gel, ethyl acetate) to obtain 24.5 g of 5-amino-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide as colorless crystals.
Workup
- filtrationCatalyst was filtered through Celite(Hyflo Super-cel) and,
- washafter washed the collected material well with ethyl acetate
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue obtained
- customwas purified by means of column chromatography (silica gel, ethyl acetate)
Sources & evidence
- ORD record
- ord-25d59156999542fc86b97840bb693afb
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706763B1
Linked notes
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