Ethyl 4-nitrophenylacetate → p-Aminophenylacetic acid ethyl ester

HRID 1460259Notes

Reaction equation

HRID 1460259 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-])=O>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 225219p-Aminophenylacetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.18 g (0.02 mole) of ethyl p-nitrophenylacetate in 200 mL of ethanol is subjected to catalytic hydrogenation. The mixture is filtered to remove the catalyst and the filtrate is concentrated to obtain quantitative yield of ethyl 4-aminophenylacetate. To an agitated solution of the ethyl 4-aminophenylacetate and 2.02 g (0.02 mole) of triethylamine in 50 ml of dimethylformamide is added dropwise a solution of 7.58 g (0.020 mole) of 1-(3-chloropropyl)-α,α-bis(4-fluorophenyl)-4-piperidinemethanol in 20 ml of dimethylformamide. After stirring at ambient temperature for 4 hr the reaction mixture is heated at 70° C. for 4 hr. The reaction mixture is concentrated and the crude product partitioned between methylene chloride and water. The methylene chloride solution is washed with water, dried over anhydrous magnesium sulfate, and concentrated to yield the title compound.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-07ae06bc3a3042fd92882956ec25651d
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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