4-Nitroaniline → 4-Nitroformanilide

HRID 437975Notes

Reaction equation

HRID 437975 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[N+:8]([C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)([O-:10])=[O:9]>C(O)=O>[N+:8]([C:11]1[CH:17]=[CH:16][C:14]([NH:15][CH:5]=[O:7])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 7918Acetic Anhydride

Product 1

HCID 853014-Nitroformanilide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a mixture of 12 ml. of formic acid and 20 ml. of acetic anhydride (which has been stirred at room temperature for 45 minutes) is added 5 g. (0.036 m.) of p-nitroaniline. After stirring for five hours at room temperature, the reaction mixture is filtered to give p-nitroformanilide, m.p. 195°-199° C. The latter, 3 g. (0.018 m.), is hydrogenated at room temperature in a mixture of 150 ml. of ethanol and 0.3 g. of 10% palladium-on-carbon in a Parr apparatus until the calculated amount of hydrogen is absorbed. The catalyst is filtered off and the solvent is removed in vacuo to leave p-aminoformanilide.

Workup

  1. additionTo a mixture of 12 ml
  2. filtrationthe reaction mixture is filtered

Sources & evidence

ORD record
ord-71cc8ced647d4de3b6ca83c8349f4682
Source dataset
uspto-grants-1977_06
Patent number
US04032652

Reaction notes

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