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

HRID 400754Notes

Reaction equation

HRID 400754 reaction equation
[CH3:1][C:2]1[C:3]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH3:15])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#N.[OH-:16].[K+].[OH2:18]>>[CH3:1][C:2]1[C:3]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH3:15])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]([OH:18])=[O:16]

Participants

4

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 673978125-Methyl-6-(2-methylpyrrolidin-1-yl)nicotinonitrile

Product 1

HCID 584433605-Methyl-6-(2-methylpyrrolidin-1-yl)nicotinic acid

Procedure

A solution of 5-methyl-6-(2-methylpyrrolidin-1-yl)nicotinonitrile obtained in step 1 (591 mg; 2.94 mmol) in water (15 mL) and KOH (823 mg; 14.68 mmol) was heated at reflux for 16 hours. Reaction mixture was basified to pH 6 and extracted with EtOAc to give the title compound as a white solid. 1H NMR (DMSO-d6) δ 12.43 (s, 1H), 8.48 (d, J=2.2 Hz, 1H), 7.74-7.73 (m, 1H), 4.41-4.32 (m, 1H), 3.81-3.73 (m, 1H), 3.49-3.42 (m, 1H), 2.29 (s, 3H), 2.10-2.04 (m, 1H), 1.94-1.88 (m, 1H), 1.74-1.68 (m, 1H), 1.59-1.52 (m, 1H), 1.25 (d, J=6 Hz, 3H). HPLC (Method A) Rt 1.45 min (Purity: 99.8%). LC/MS (Method B): 221.2 (M+H)+.

Workup

  1. temperatureat reflux for 16 hours
  2. customReaction mixture
  3. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-8576a99cac954de6a4f433efd354dfd6
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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