Citric Acid → 2-Amino-3-nitrobenzoic acid

HRID 1470653Notes

Reaction equation

HRID 1470653 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11]C(=O)[C:9]2=[O:14])([O-:3])=[O:2].OO.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:20]>[OH-].[Na+]>[NH2:11][C:12]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=1[C:9]([OH:14])=[O:20]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 784Hydrogen PeroxideHCID 38583087-nitroisatin

Product 1

HCID 2196332-Amino-3-nitrobenzoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a ice cold solution of 7-nitro-1H-indole-2,3-dione (9 g, 47 mmol) in 2 M aqueous sodium hydroxide (50 mL), an aq. solution of 30% hydrogen peroxide (9 mL) was added drop wise. The mixture was warmed to room temperature and stirred overnight. The resulting mixture was carefully acidified by the addition of an aq. saturated citric acid solution. The solid precipitate was collected by filtration, washed with water and dried in a vacuum oven to get 6 g of the required product as a yellow coloured solid (70%).

Workup

  1. filtrationThe solid precipitate was collected by filtration
  2. washwashed with water
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-f5f2da426de24df18e2ee56633533e4e
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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