Hydrochloric Acid → 2-Amino-4-chloro-3-methylbenzoic acid

HRID 251937Notes

Reaction equation

HRID 251937 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6](=[O:13])C(=O)[NH:8]2)=[CH:4][CH:3]=1.[OH-:14].[Na+].OO.Cl>>[NH2:8][C:9]1[C:10]([CH3:11])=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:6]([OH:13])=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 45130676-chloro-7-methyl-1H-indole-2,3-dione

Product 1

HCID 8274632-Amino-4-chloro-3-methylbenzoic acid

Procedure

A mixed solution of 1.3 g of 6-chloro-7-methyl-1H-indole-2,3-dione and 50 ml of a 2N aqueous sodium hydroxide solution was added dropwise to 2 g of aqueous hydrogen peroxide (30%), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was adjusted to pH 4 by an addition of 2N hydrochloric acid, and a deposited precipitate was collected by filtration to obtain 0.6 g of 2-amino-4-chloro-3-methylbenzoic acid of the formula:

Workup

  1. filtrationa deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-01ff3a7288eb400990df86a651eee702
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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