2-Pyridin-3-yl-butyric acid ethyl ester → 2-(Pyridin-3-yl)butanoic acid

HRID 401599Notes

Reaction equation

HRID 401599 reaction equation
C([O:3][C:4](=[O:14])[CH:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][CH3:7])C>Cl>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH:5]([CH2:6][CH3:7])[C:4]([OH:14])=[O:3])[CH:9]=1

Participants

3

Reactant 1

HCID 580329722-Pyridin-3-yl-butyric acid ethyl ester

Product 1

HCID 179099082-(Pyridin-3-yl)butanoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-Pyridin-3-yl-butyric acid ethyl ester (8 g, 0.04 mol) and a 20% aqueous solution of hydrochloric acid (50 mL) was heated to reflux for 3 hours. The solvent evaporated to dryness to yield the desired product (5 g, 0.02 mol, 50%), ESI-MS m/z calc. 165.1. found 166.5 (M+1)+ 1H NMR (DMSO-d6): δ 8.86 (s, 1H), 8.80 (d, 1H, J=5.6 Hz), 8.47 (d, 1H, J=8.0 Hz), 7.97 (dd, 1H, J=5.6, 8.0 Hz), 3.83 (t, 1H, J=8.0 Hz), 2.07-2.04 (m, 1H), 1.82-1.80 (m, 1H), 0.80 (t, 3H, J=7.6 Hz).

Workup

  1. temperatureto reflux for 3 hours
  2. customThe solvent evaporated to dryness

Sources & evidence

ORD record
ord-a66bbda2960d474e966172df26a7577a
Source dataset
uspto-grants-2014_06
Patent number
US08741939B2

Reaction notes

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