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

HRID 1512455Notes

Reaction equation

HRID 1512455 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 compound ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate (10 g), in dry MeOH (100 mL), Pd(OH)2 (2 g) was added and the mixture was reduced under an H2 atmosphere for 6 h at room temperature. The mixture was filtered a pad of Celite™ washing with MeOH. The combined filtrates were concentrated under reduced pressure to yield ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetate (7.5 g) as a thick liquid. 1H-NMR (CDCl3, 200 MHz): 0.38 (m, 2H), 0.61 (m, 2H), 1.23 (m, 1H), 1.23 (t, 3H), 3.51 (s, 2H), 3.80 (d, 2H), 4.16 (q, 2H), 6.72 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-3d6fdb4711bc41f19d19e43b862e0cde
Source dataset
uspto-grants-2012_07
Patent number
US08217064B2

Reaction notes

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