Hydrochloric Acid → 6-(Propan-2-yl)pyridine-2-carboxylic acid

Concentrated hydrochloric acid (15 mL) was added to a solution of 6-isopropylpicolinonitrile (example 85, step c) (1.23 g) in methanol (30 mL). The resulting mixture was heated at reflux for 17 h and allowed to cool to RT. The mixture was cautiously poured into sodium hydroxide solution (10M, 50 mL) and stirred at RT overnight. The reaction was concentrated and the pH adjusted to 5 using 2M HCl solution. The aqeuous mixture was extracted with chloroform (3×100 mL). The organic solutions were combined, washed with brine (100 mL), dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a yellow oil. Yield 0.94 g.

1. temperatureThe resulting mixture was heated
2. temperatureat reflux for 17 h
3. concentrationThe reaction was concentrated
4. extractionThe aqeuous mixture was extracted with chloroform (3×100 mL)
5. washwashed with brine (100 mL)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. customevaporated

ORD record

ord-49472284702e40fb9f858e839ae21438

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2