Ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate → Ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetate

HRID 1183734Notes

Reaction equation

HRID 1183734 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:10][C:11]=2[N+:12]([O-])=O)[CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[NH2:12][C:11]1[CH:10]=[CH:9][C:8]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7][C:6]=1[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57995474Ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate

Product 1

HCID 57995628Ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetateYield 84%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate (10 g), in dry MeOH (100 mL) was added Pd(OH)2 (2 g). The mixture was hydrogenated under a H2 atmosphere for 6 h at room temperature. The reaction mixture was filtered through a pad of Celite™, washing with MeOH. The combined filtrates were concentrated under reduced pressure to yield 7.5 g of the desired product as an oil.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite™
  2. washwashing with MeOH
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-7f94870a57214281b774602e60e96ba7
Source dataset
uspto-grants-2014_03
Patent number
US08664249B2

Reaction notes

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