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

HRID 250855Notes

Reaction equation

HRID 250855 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH:16]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH:16]=1

Participants

4

Reactant 1

HCID 67272864methyl(E)-3-(2-methoxy-3'-methylaminobiphenyl-4-yl)acrylate

Product 1

HCID 67273007Methyl 3-(2-methoxy-3'-methylaminobiphenyl-4-yl)propanoateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

100 mg (18% by mass) of 10% palladium-on-charcoal are added to a solution of 560 mg (1.88 mmol, 1 eq) of methyl (E)-3-(2-methoxy-3′-methylaminobiphenyl-4-yl)acrylate in 10 ml of methanol. The reaction mixture is stirred at room temperature under a hydrogen atmosphere for 4 hours. The reaction medium is filtered through Celite and then evaporated to dryness. 495 mg of methyl 3-(2-methoxy-3′-methylaminobiphenyl-4-yl)propanoate are obtained in oil form. Yield=88%

Workup

  1. filtrationThe reaction medium is filtered through Celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-6be657c6477b4221a6cc8a8df39414a7
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

Loading…