Formic Acid → N-[4-methoxy-3-(trifluoromethyl)benzyl]formamide
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[CH:15]([NH2:17])=[O:16].C(O)=O.O>C(OCC)(=O)C>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:5]([CH2:6][NH:17][CH:15]=[O:16])=[CH:4][C:3]=1[C:2]([F:14])([F:13])[F:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 5.8 g 3-trifluoromethyl-p-anisaldehyde, 8.6 ml formamide, and 13.6 ml formic acid was stirred at 130° C. for 9 hr. After cooling, water and ethyl acetate were added thereto. The ethyl acetate layer was recovered and washed with brine. It was dried over anhydrous magnesium sulfate, filtered, and evaporated. The resulting residue was purified by silica gel column chromatography to give 3.8 g of N-[4-methoxy-3-(trifluoromethyl)benzyl]formamide.
Workup
- temperatureAfter cooling
- customThe ethyl acetate layer was recovered
- washwashed with brine
- dry with materialIt was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-6687c211faa74f90ad4a2435468d95bf
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498159B1
Reaction notes
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