Ammonium Hydroxide → 2-Amino-3-chlorobenzoic acid

HRID 325492Notes

Reaction equation

HRID 325492 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][C:10]1[C:11]([N+:19]([O-])=O)=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14].[OH-].[NH4+]>O>[Cl:9][C:10]1[C:11]([NH2:19])=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 209023-Chloro-2-nitrobenzoic acidHCID 24489Sodium Dithionite

Product 1

HCID 808072-Amino-3-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium dithionite (104.4 g, 0.6 m) in water (400 ml) was added in portions to a slurry of 3-chloro-2-nitrobenzoic acid (30 g, 0.15 m) in water (200 ml) containing concentrated ammonium hydroxide solution (10 ml). After stirring an additional 20 minutes the mixture was filtered, acidified to pH 3-4 with concentrated hydrochloric acid and filtered again. The filtrate was saturated with sodium chloride and extracted with ether. Drying and concentration of the extract gave a white powder which was combined with the precipitates above. The crude product was used without further purification.

Workup

  1. filtrationwas filtered
  2. filtrationfiltered again
  3. extractionextracted with ether
  4. customDrying
  5. customconcentration of the extract gave a white powder which
  6. customprecipitates above
  7. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-0e6e681566be4e11bbbe063b56dd0100
Source dataset
uspto-grants-1984_04
Patent number
US04440941

Reaction notes

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