Methyl 2-(2-nitrophenyl)acetate → Methyl 2-aminobenzeneacetate

HRID 2200162Notes

Reaction equation

HRID 2200162 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 520464Methyl 2-(2-nitrophenyl)acetate

Product 1

HCID 5743389Methyl 2-aminobenzeneacetateYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add Pd/C (10%, 800 mg) to a solution of methyl 2-(2-nitrophenyl)acetate (7.5 g, 38.5 mmol) in methanol (50 mL) under N2, then flush with H2, stir the reaction under H2 atmosphere at room temperature overnight. Remove the hydrogen; filter off the solid, concentrate the filtrate under reduced pressure to obtain the crude product (4.8 g, 76.2%) which is used directly without further purification. MS: (M+1):166.

Workup

  1. customflush with H2
  2. customthe reaction under H2 atmosphere at room temperature overnight
  3. customRemove the hydrogen
  4. filtrationfilter off the solid
  5. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-dc5f030c8a6849da8567e28dd1ee45c6
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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