Ammonium Chloride → Methyl 4-amino-3-methylbenzoate

HRID 626209Notes

Reaction equation

HRID 626209 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[C:5]([O:7][CH3:8])=[O:6].[NH4+].[Cl-]>CO.O.[Fe]>[NH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[CH3:1]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 260927Methyl 3-methyl-4-nitrobenzoate

Product 1

HCID 2736799Methyl 4-amino-3-methylbenzoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 23925IronSolvent

Procedure

To a stirred solution of methyl 3-methyl-4-nitrobenzoate (50 g, 1.0 eq) in 1 L MeOH were added at rt a solution of NH4Cl (137 g, 10 eq) in 60 mL H2O and Fe power (96 g, 7 eq), and the resulting mixture is heated at reflux for 4 h. The reaction mixture was allowed to cool to rt, filtered, and water was added. The mixture was extracted with EtOAc. The extract was dried, washed with water, and concentrated to give the desired product directly as a white solid (26 g, 62%).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 4 h
  3. filtrationfiltered
  4. additionwater was added
  5. extractionThe mixture was extracted with EtOAc
  6. customThe extract was dried
  7. washwashed with water
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3a3f1033d929483f89b7524f2915eba8
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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