Ammonium Hydroxide → 3-Methyl-2-nitroaniline

HRID 1995135Notes

Reaction equation

HRID 1995135 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)C(O)=O.[N-:14]=[N+]=[N-].[Na+].[OH-].[NH4+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[NH2:14]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 215753-Methyl-2-nitrobenzoic acidHCID 33557Sodium Azide

Product 1

HCID 690383-Methyl-2-nitroanilineYield 99.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A stirred solution of 3-methyl-2-nitrobenzoic acid (18.1 g, 0.1 mole) in 150 ml of concentrated sulfuric acid was cooled to -5°. Sodium azide (7.5 g, 0.115 mole) was added portionwise to the reaction mixture. After complete addition the reaction mixture was heated at 55° for three hours, then stirred at room temperature for two days. The reaction mixture was poured into ice water and the resulting solution made alkaline (pH 9) with concentrated ammonium hydroxide. A solid precipitate formed and was collected by filtration to give 3-methyl-2-nitroaniline (15.1 g, mp 105°-108.5°).

Workup

  1. additionAfter complete addition the reaction mixture
  2. temperaturewas heated at 55° for three hours
  3. customA solid precipitate formed
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1538ed44a25c4ac1a109b0238ac990d4
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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