Water → 5-Methyl-6-(2-methylpiperidin-1-yl)nicotinic acid

HRID 400738Notes

Reaction equation

HRID 400738 reaction equation
[CH3:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#N.[OH-:17].[K+].[OH2:19]>>[CH3:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]([OH:19])=[O:17]

Participants

4

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 674005855-Methyl-6-(2-methylpiperidin-1-yl)nicotinonitrile

Product 1

HCID 584433645-Methyl-6-(2-methylpiperidin-1-yl)nicotinic acid

Procedure

A solution of 5-methyl-6-(2-methylpiperidin-1-yl)nicotinonitrile obtained in step 1 (1.0 g; 4.64 mmol) and KOH (1.3 g; 23.22 mmol) in water (60 mL) was heated at reflux for 16 hours. After this time, reaction mixture was acidified to pH 3 and extracted with EtOAc to give the title compound as a yellow solid (1.1 g, quantitative). 1H NMR (DMSO-d6) δ 12.82 (bs, 1H), 8.58 (d, J=2.3 Hz, 1H), 7.88 (d, J=2.3 Hz, 1H), 3.85-3.82 (m, 1H), 3.19-3.10 (m, 2H), 2.24 (s, 3H), 1.75-1.44 (m, 6H), 1.04 (d, J=6.2 Hz, 3H). HPLC (Method B) Rt 1.96 min (Purity: 92.2%). LC/MS (Method A): 235.2 (M+H)+.

Workup

  1. temperatureat reflux for 16 hours
  2. customAfter this time, reaction mixture
  3. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-f306c2ac73d64eaba7fdb9dacd72060b
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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