Hydrochloric Acid → 2-Amino-3-nitrobenzoic acid

HRID 1736725Notes

Reaction equation

HRID 1736725 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[NH4+:15].Cl>O.[Cu]Cl>[NH2:15][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 198702-Chloro-3-nitrobenzoic acid

Product 1

HCID 2196332-Amino-3-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

A solution of 2-chloro-3-nitrobenzoic acid (5.00 g, 24.8 mmol), ammonium hydroxide (25.0 ml) and copper (1) chloride (50 mg) is heated hi a bomb at 125° for 20 hr and is then allowed to cool to 20°-25°. The solid residue is dissolved in water and the solution acidified with 3 N hydrochloric acid. The resultant mixture is filtered, washed, and dried to provide the 2-amino-3-nitrobenzoic acid, mp 201°-203; IR (mineral oil) 3478, 3345, 2954, 2925, 2855, 1692, 1677, 1571, 1559, 1520, 1512, 1442, 1271, 1259, 1130 cm-1 ; NMR (300 MHz, CDCl3 -MeOD) 8.38, 8.30, 6.66; MS (EI) m/e 182, 164.

Workup

  1. temperatureto cool to 20°-25°
  2. filtrationThe resultant mixture is filtered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-8d6c28ae8c084addba44031389e32f2c
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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