Reaction #595328

Reaction equation

HCl

MeOH

LiOH

ethyl 4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

→

title compound

Yield 100.0%

4-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Yield 100.0%

Solvents

THF

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (30 mL×3)
2. 2
   WashThe combined organic layers were washed with brine (30 mL)
3. 3
   Dryingdried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under the reduced pressure

Procedure

To a solution of ethyl 4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate (172 mg, 0.75 mmol) dissolved in a 4:1 mixture of THF:MeOH (5 mL) (v:v), was added a aqueous solution of LiOH (1.52 mmol, 1M). After stirring for 40 min, the reaction mixture was acidified to pH ˜1 with HCl(1N, aq) and extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine (30 mL), dried (MgSO4), filtered and concentrated under the reduced pressure to give an off-white solid as the title compound. (163 mg, 100% yield). MW m/z: 202.3 (MW+1), 204.2 (MW+1+Cl pattern); 200.4 (MW−1), 202.4 (MW−1+Cl pattern). 1H NMR (DMSO-d6, 300 Hz): δ ppm 12.97 (s, 1H), 8.42 (s, 1H), 3.48 (s, 3H), 2.10 (s, 3H).

Source