Acetamide, N-(2-methyl-4-nitrophenyl)- → 2-Methyl-6-nitroaniline

HRID 1493544

Reaction equation

HRID 1493544 reaction equation
C([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:14])(=O)C.C(NC1C=CC([N+]([O-])=O)=CC=1C)(=O)C>>[NH2:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:14]

Participants

3

Reactant 2

HCID 75936Acetamide, N-(2-methyl-4-nitrophenyl)-HCID 316249N-(2-methyl-6-nitrophenyl)acetamide

Product 1

HCID 112982-Methyl-6-nitroanilineYield 46%

Procedure

The wet mixture of 2-acetylamino-3-nitrotoluene (4) and 2-acetylamino-5-nitrotoluene as obtained in Preparation Example 1 was placed in a steam distillation apparatus, and 300 ml of concentrated hydrochloric acid was added thereto. Immediately on heating and boiling, the mixture was hydrolyzed. The boiling was continued until 36 l of a distillate was collected. On cooling the distillate, there was obtained 2-amino-3-nitrotoluene (5) as an orange needle-like crystal having a melting point of 92.8° to 93.2° C. and a 46% yield.

Workup

  1. customas obtained in Preparation Example 1
  2. distillationwas placed in a steam distillation apparatus, and 300 ml of concentrated hydrochloric acid
  3. additionwas added
  4. temperatureImmediately on heating
  5. customwas collected
  6. temperatureOn cooling the distillate, there

Sources & evidence

ORD record
ord-7b49919bcd514aa6b4eb47578b0c1942
Source dataset
uspto-grants-1991_06
Patent number
US05021593

Linked notes

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