Hydrochloric Acid → 2-amino-5-methyl-3-nitrobenzoic acid

HRID 1470604Notes

Reaction equation

HRID 1470604 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7]C(=O)[C:5]2=[O:15].[OH:16]O.Cl>[OH-].[Na+].O>[NH2:7][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=1[C:5]([OH:15])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 10330598HCID 10330598, compound

Product 1

HCID 2319842-amino-5-methyl-3-nitrobenzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-methyl-7-nitro-1H-indole-2,3-dione (6.5 g, 0.0315 mol) in 2N NaOH (35 mL) was cooled to 20° C. and a 30% aq. solution of H2O2 (6.5 mL) was added slowly over a period of 15 min. The reaction mixture was brought to room temperature and stirred for 12 h, then diluted with water (75 mL). The pH was adjusted to 2 with conc. HCl. The formed precipitate was filtered and dried in a vacuum oven to get 5.3 g of the required product as a yellow coloured solid (85%).

Workup

  1. customwas brought to room temperature
  2. filtrationThe formed precipitate was filtered
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-94252a1db57641aab5541de79cd633d6
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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