Ammonium Chloride → Methyl 3-amino-5-chloro-2-hydroxybenzoate

HRID 329717Notes

Reaction equation

HRID 329717 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([OH:14])=[C:6]([N+:15]([O-])=O)[CH:5]=1>C1(C)C=CC=CC=1.[Fe]>[NH2:15][C:6]1[CH:5]=[C:4]([Cl:3])[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=1[OH:14]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 235651methyl 5-chloro-2-hydroxy-3-nitrobenzoate

Product 1

HCID 687991Methyl 3-amino-5-chloro-2-hydroxybenzoateYield 59.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

To 100 ml of an aqueous 0.78N ammonium chloride solution (with heating at 85° C.) is added 33.4 g of powdery iron with stirring followed by addition of a solution of 49.1 g of methyl 5-chloro-3-nitrosalicylate in 500 ml of toluene over 30 minutes. The reaction temperature rises to 95° C. The resultant solution is stirred at 80°-90° C. for an hour, and filtered with suction through hot celite. The mother liquor is poured into 1 l of ice-cold water, and the toluene layer is separated, washed with water and dried over magnesium sulfate. The solvent is distilled off and the residue is recrystallized from ethanol to give 25.4 g of methyl 3-amino -5-chlorosalicylate, melting at 65°-67° C.

Workup

  1. customrises to 95° C
  2. filtrationfiltered with suction through hot celite
  3. additionThe mother liquor is poured into 1 l of ice-cold water
  4. customthe toluene layer is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-592faf66c2b74c0d9956e5cc2227089b
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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