methyl(E)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)acrylate → Methyl 3-(2-butoxy-3'-methylaminobiphenyl-4-yl)propanoate

HRID 250922Notes

Reaction equation

HRID 250922 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[CH:13]/[C:14]([O:16][CH3:17])=[O:15])[CH:9]=[CH:8][C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][CH3:25])[CH:19]=1)[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:9]=[CH:8][C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][CH3:25])[CH:19]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 67272862methyl(E)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)acrylate

Product 1

HCID 67273032Methyl 3-(2-butoxy-3'-methylaminobiphenyl-4-yl)propanoateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3.63 g (10.7 mmol) of methyl (E)-3-(2-butoxy-3′-methylaminobiphenyl-4-yl)acrylate in 70 ml of methanol is stirred for 4 hours at room temperature in the presence of 363 mg (10% by mass) of 10% palladium-on-charcoal under a hydrogen atmosphere. The palladium is filtered off and the solvent is evaporated off. 3.39 g of methyl 3-(2-butoxy-3′-methylaminobiphenyl-4-yl)propanoate are obtained in the form of a yellowish oil. Yield=93%

Workup

  1. filtrationThe palladium is filtered off
  2. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-2fbd068e1be348f6baf7fbcdc9c6eb92
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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