Formic Acid → N-(6-Methylpyridin-2-yl)formamide

Temperature

70 °C

To stirred neat formic acid (3.83 mL, 101.7 mmol) was added acetic anhydride (6.98 mL, 74.0 mmol). The reaction mixture was heated under stirring at 70° C. for 2 hrs and allowed to room temperature. A solution of 6-methylpyridin-2-amine (5.00 g, 46.23 mmol) in tetrahydrofurane (30 mL), was added dropwise in order to prevent temperature from rising above 45° C. The reaction mixture was allowed to room temperature and stirred for further 1 hr. The reaction mixture was concentrated in vacuo and the residue was diluted in 100 mL of ethanol. The reaction mixture was stirred for 2 hrs at room temperature concentrated in vacuo, yielding to N-(6-methylpyridin-2-yl)formamide as a yellow solid [2.00 g, yield 32%; HPLC/MS: m/z=137 (M+H); logP(HCOOH)=0.45].

1. temperatureThe reaction mixture was heated
2. customallowed to room temperature
3. customfrom rising above 45° C
4. customwas allowed to room temperature
5. stirringstirred for further 1 hr
6. concentrationThe reaction mixture was concentrated in vacuo
7. additionthe residue was diluted in 100 mL of ethanol
8. stirringThe reaction mixture was stirred for 2 hrs at room temperature
9. concentrationconcentrated in vacuo

ORD record

ord-d2e99765231c47cb9fba30d7098bbbb3

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2