Dichloromethane → Methyl 3-(2-methoxy-5-pyridyl)propionate

HRID 474755Notes

Reaction equation

HRID 474755 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1.C(Cl)Cl>[Pd].CCO>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 53929170Methyl beta-(2-methoxypyridin-5-yl)acrylate

Product 1

HCID 22009636Methyl 3-(2-methoxy-5-pyridyl)propionateYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3-(6-methoxy-pyridin-3-yl)-acrylic acid methyl ester (1.2 g, 6.21 mmol, 1 eq) and Pd/C, 10% (330 mg, 0.05 eq, 10%) was stirred in a DCM (15 ml)/absolute EtOH (15 ml) solvent mixture under hydrogen atmosphere for 1 hour at room temperature. Palladium was filtered off over a celite pad, the solvent was evaporated and obtained was 3-(6-methoxy-pyridin-3-yl)-propionic acid methyl ester (1.18 g, yield=93%, purity=95%) in form of yellowish oil. MS: [M+H]+=196.15 1H NMR (300 MHz; CDCl3) δ/ppm 2.59 (t, J=7.75 Hz, 2H), 2.88 (t, J=7.75 Hz, 2H), 3.67 (s, 3H), 3.91 (s, 3H), 6.68 (d, J=8.46 Hz, 1H), 7.42 (dd, J=7.42 Hz, J=2.40 Hz, 1H), 8.00 (d, J=2.40 Hz, 1H)

Workup

  1. filtrationPalladium was filtered off over a celite pad
  2. customthe solvent was evaporated
  3. customobtained

Sources & evidence

ORD record
ord-14e3133e3af64597a0cec5ba5b5d1a76
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

Loading…