Acetic Acid → 3-(2-Amino-4-chloro-phenoxy)-cyclopentanecarboxylic acid ethyl ester

HRID 1773526Notes

Reaction equation

HRID 1773526 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[N+:19]([O-])=O)[CH2:7]1)=[O:5])[CH3:2].C(O)(=O)C>ClCCl.[Zn]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[NH2:19])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 580562213-(4-Chloro-2-nitro-phenoxy)-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 580563063-(2-Amino-4-chloro-phenoxy)-cyclopentanecarboxylic acid ethyl esterYield 79%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-chloro-2-nitro-phenoxy)-cyclopentanecarboxylic acid ethyl ester (280 mg) in dichloromethane (20 mL) was added zinc dust (2 g) followed by glacial acetic acid (1 mL) and the resulting mixture was stirred at room temperature for 20 minutes. The solid was filtered, washed with dichloromethane and discarded. The filtrate was evaporated under reduced pressure and the residue was purified by flash chromatography (hexane/acetone, 80/20) to afford 200 mg of 3-(2-amino-4-chloro-phenoxy)-cyclopentanecarboxylic acid ethyl ester.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with dichloromethane
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by flash chromatography (hexane/acetone, 80/20)

Sources & evidence

ORD record
ord-4ed4226b9743412793a2e972f4396853
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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