Methanol → HCID 68957309, compound

HRID 2191642Notes

Reaction equation

HRID 2191642 reaction equation
CO.[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:11]=[CH:12]/[C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([N+:26]([O-])=O)[CH:14]=2)[CH:8]=[CH:9][CH:10]=1>[C].[Pd].C(OCC)(=O)C>[NH2:26][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=2)[CH:25]=[CH:24][C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

5

Reactant 2

HCID 887MethanolHCID 67342987HCID 67342987, compound

Product 1

HCID 68957309HCID 68957309, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of methanol 22 mL and ethyl acetate 22 mL of tert-butyl 4-((E)-2-(3-methoxyphenyl)vinyl)-2-nitrobenzoate 2.2 g was added 10% palladium-carbon 0.66 g, and it was stirred under hydrogen atmosphere at room temperature for 2 hours. The solvent was removed under reduced pressure after insoluble matter was filtrated. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=8:1] to give tert-butyl 2-amino-4-(2-(3-methoxyphenyl)ethyl)benzoate 1.6 g of colorless oil.

Workup

  1. customThe solvent was removed under reduced pressure after insoluble matter
  2. filtrationwas filtrated

Sources & evidence

ORD record
ord-9f0fcde26b594a5ea700913ce5cbd0de
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

Loading…