Formic Acid → 71894-91-2

HRID 1110803Notes

Reaction equation

HRID 1110803 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH:12](O)=[O:13].C(OC(=O)C)(=O)C>C(Cl)Cl>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:12]=[O:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 69784-Methyl-2-nitroanilineHCID 7918Acetic Anhydride

Product 1

HCID 345693771894-91-2Yield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methyl-2-nitroaniline, 30 g (197 mmols), was dissolved in 500 ml of methylene chloride and a liquid mixture of 52 ml (1.378 mol) of formic acid and 31 ml (328 mmols) of acetic anhydride was added dropwise to the solution. The mixture was stirred at room temperature for 16 hours. The solvent was distilled off under reduced pressure. The resulting crystals were washed with ether to give 34.7 g (97.7%) of N-(4-methyl-2-nitrophenyl)formamide.

Workup

  1. additionwas added dropwise to the solution
  2. distillationThe solvent was distilled off under reduced pressure
  3. washThe resulting crystals were washed with ether

Sources & evidence

ORD record
ord-8beae2cf9b994b43981ab2bfb49105fa
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

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