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

HRID 1370995Notes

Reaction equation

HRID 1370995 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 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-nitrophenylacetate (10.1 g, 51.2 mmol) in 125 mL of methanol containing 221 mg of 10% Pd/C was placed on the Parr hydrogenator at 40 psi. After 5 h the mixture was filtered through celite and evaporated under reduced pressure to give a clear red oil. The solvent was evaporated under reduced pressure to give 8.5 g (100%) of methyl 2-aminophenylacetate as a clear red oil. TLC (silica, EtOAc/hexanes): Rf=0.24. 1H NMR (400 MHz, CDCl3): 7.21 (m, 2H), 6.86 (m, 2H), 3.81 (s, 3H), 3.70 (s, 2H).

Workup

  1. filtrationAfter 5 h the mixture was filtered through celite
  2. customevaporated under reduced pressure
  3. customto give a clear red oil
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-03fdc31774d643189fa95400874e02d0
Source dataset
uspto-grants-2003_06
Patent number
US06583155B2

Reaction notes

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