Ammonia → 4-Nitroaniline

HRID 1729117Notes

Reaction equation

HRID 1729117 reaction equation
N.[N+:2]([C:5]1[CH:19]=[CH:18][C:8]([NH:9]C(=O)C2C=CC=CC=2)=[CH:7][CH:6]=1)([O-:4])=[O:3].C(N)(=O)C1C=CC=CC=1>CO>[N+:2]([C:5]1[CH:19]=[CH:18][C:8]([NH2:9])=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 2331BenzamideHCID 769304'-Nitrobenzanilide

Product 1

HCID 74754-NitroanilineYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

Approximately 10 ml of liquid ammonia was added rapidly to a solution of 100 mg of 4'-nitrobenzanilide and 50 ml of methanol in a Parr bomb at -50° C. The Parr reactor was stirred at 120° C./300 psi (21.1 kg/cm2) for 3 days. After the reactor was cooled to -50°C., the pressure was released and the reactor was opened. An aliquot was taken out for HPLC analysis which revealed a 50% yield of 4-nitroaniline and benzamide. The remainder of the material was unreacted.

Workup

  1. temperatureAfter the reactor was cooled to -50°C.

Sources & evidence

ORD record
ord-c9dcf08f15d24adda6480693506c057c
Source dataset
uspto-grants-1994_07
Patent number
US05331099

Reaction notes

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