3-Quinolin-6-yl-acrylic acid ethyl ester → Ethyl 3-(6-quinolinyl)propanoate

HRID 655205Notes

Reaction equation

HRID 655205 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)[CH3:2]

Participants

4

Reactant 1

HCID 685315143-Quinolin-6-yl-acrylic acid ethyl ester

Product 1

HCID 23003951Ethyl 3-(6-quinolinyl)propanoateYield 49.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-quinolin-6-yl-acrylic acid ethyl ester (200 mg, 0.881 mmol) and 10% wt Pd/C (93 mg, 0.088 mmol) in methanol (3 mL) was stirred at room temperature under hydrogen atmosphere for 3 h. Mixture was filtered through celite and the filtrate was absorbed on silica gel. Purification on silica gel with 0-65% gradient of ethyl acetate in hexane provided 100 mg of product as a clear oil. 1H NMR 500 MHz (DMSO) δ 1.13 (t, 3H), 2.74 (t, 2H), 3.05 (t, 2H), 4.04 (q, 2H), 7.50 (dd, 1H), 7.67 (dd, 1H), 7.78 (d, 1H), 7.94 (d, 1H), 8.29 (dd, 1H), 8.84 (dd, 1H); MS (m/z) 230 [M+H+]+.

Workup

  1. filtrationMixture was filtered through celite
  2. customthe filtrate was absorbed on silica gel
  3. customPurification on silica gel with 0-65% gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-b199d8f8c4ea49cfb62213ffad662d58
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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