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Formic Acid → N-[4-methoxy-3-(trifluoromethyl)benzyl]formamide

HRID 2300131
Notes
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Reaction equation

HRID 2300131 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 284Formic AcidHCID 713FormamideHCID 962WaterHCID 27752914-Methoxy-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 22744421N-[4-methoxy-3-(trifluoromethyl)benzyl]formamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. temperatureAfter cooling
  2. customThe ethyl acetate layer was recovered
  3. washwashed with brine
  4. dry with materialIt was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6687c211faa74f90ad4a2435468d95bf
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06498159B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes