Ethyl 1-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)cyclobutanecarboxylate → Ethyl 1-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)cyclobutanecarboxylate

HRID 1512480Notes

Reaction equation

HRID 1512480 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[O:19][CH2:20][C:21]([F:24])([F:23])[F:22])([O-])=O>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[O:19][CH2:20][C:21]([F:22])([F:23])[F:24]

Participants

4

Reactant 1

HCID 57995578Ethyl 1-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)cyclobutanecarboxylate

Product 1

HCID 57995647Ethyl 1-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)cyclobutanecarboxylateYield 97.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 1-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)cyclobutanecarboxylate (900 mg), in dry MeOH (50 mL), Pd(OH)2 (400 mg) was added and the mixture reduced under an atmosphere of H2 for 6 h at room temperature. The mixture was filtered through a pad of Celite™ washing with MeOH, the combined filtrates were concentrated under reduced pressure to yield ethyl 1-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)cyclobutanecarboxylate (800 mg) as a thick liquid.

Workup

  1. filtrationThe 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-21134240e4f14550b8a5963a7a90d263
Source dataset
uspto-grants-2012_07
Patent number
US08217064B2

Reaction notes

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