Methanol → Methyl 6-methylnicotinate

A solution of 6-methyl nicotinic acid, 2-1 (5 g, 36.5 mmol) in 100 ml of anhydrous methanol was placed in a 250 ml three neck flask equipped with a dropping funnel vertical condenser and CaCl2 drying tube. The reaction solution was cooled to -15° in an ice acetone bath and SOCl2 (5 ml, 69.1 mmol) was added dropwise. The solution was then heated at reflux for 3 h then cooled and the solvent removed at reduced pressure. The resulting white solid was treated with 60 ml of saturated NaHCO3 and extracted into CH2Cl2 (3×50 ml). The pooled extracts were dryed (Na2SO4 ), filtered and evaporated at reduced pressure. The resulting oil crystallized on standing giving 2-2 as a white solid.

1. customequipped with a dropping funnel vertical condenser and CaCl2 drying tube
2. temperatureThe reaction solution was cooled to -15° in an ice acetone bath
3. temperatureThe solution was then heated
4. temperatureat reflux for 3 h
5. temperaturethen cooled
6. customthe solvent removed at reduced pressure
7. additionThe resulting white solid was treated with 60 ml of saturated NaHCO3
8. extractionextracted into CH2Cl2 (3×50 ml)
9. filtrationfiltered
10. customevaporated at reduced pressure
11. customThe resulting oil crystallized

ORD record

ord-9d12c9f111ea4483b0514385f941c999

Source dataset

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05821241