Carbon Dioxide → 3-(6-Chloropyridin-3-yl)-2-methylpropanoic acid

HRID 1714417Notes

Reaction equation

HRID 1714417 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9](C)([C:13](O)=O)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C(=O)=O>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 280Carbon DioxideHCID 542838152-[(6-Chloropyridin-3-yl)methyl]-2-methylmalonic acid

Product 1

HCID 540894253-(6-Chloropyridin-3-yl)-2-methylpropanoic acidYield 95%

Conditions

Temperature
185 °C

Procedure

The solid 2-[(6-chloropyridin-3-yl)methyl]-2-methylmalonic acid (8.70 g, 37.5 mmol) in a 500 mL round bottom flask was immersed in an oil bath heated to 185° C. As the solid melted carbon dioxide evolution occurred. After heating for 30 min, the reaction was deemed complete. Upon cooling there was obtained an amber gum (6.8 g, 95% yield). [M+H]+=200, 202; IR: 1703 (C═O). The product was about 85% pure and was used for the next step reaction directly.

Workup

  1. temperatureAfter heating for 30 min
  2. temperatureUpon cooling there

Sources & evidence

ORD record
ord-fd6b72532dbd436fa48f37ff3379af22
Source dataset
uspto-grants-2010_09
Patent number
US07795456B2

Reaction notes

Loading…