Ethyl Acetate → Ethyl 2-amino-5-phenoxybenzoate

HRID 2099973Notes

Reaction equation

HRID 2099973 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-])=O.CCOC(C)=O>CO.[Pd]>[NH2:1][C:4]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 57796884Ethyl 2-nitro-5-phenoxybenzoate

Product 1

HCID 57796887Ethyl 2-amino-5-phenoxybenzoateYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 43A (3.35 g, 11.7 mmol) in MeOH (30 mL):EtOAc (30 mL) was degassed with argon for 30 minutes. The resulting solution was treated with 10% Pd/C (335 mg) and stirred under a hydrogen atmosphere for 2 hours. The reaction mixture was filtered through a pad of celite and concentrated to afford 43B (2.6 g, 87%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b00cdc49d6cb42249c2288e72e1949fa
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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