Hydrochloric Acid → Methyl 6-aminonicotinate

Temperature

25 °C

A mixture of 6-aminonicotinic acid (4.0 g, 28.9 mmol), methanol (75 mL), and concentrated hydrochloric acid (4 mL) was heated under reflux for 16 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The resulting solid was treated with water (20 mL) and enough sodium bicarbonate to adjust the pH to pH=8. The solution was then extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 6-aminonicotinic acid methyl ester (3.12 g, 71%) as white foam: EI-HRMS m/e calcd for C7H8N2O2 (M+) 152.0586, found 152.0586.

1. temperaturewas heated
2. temperatureunder reflux for 16 h
3. concentrationconcentrated in vacuo
4. customto remove methanol
5. additionThe resulting solid was treated with water (20 mL) and enough sodium bicarbonate
6. extractionThe solution was then extracted with ethyl acetate (3×25 mL)
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-e7e5917e186e4c73ad6f9b3016ac18a4

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105671B2