Pyridine → N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide

5-Amino-2-methoxy pyridine (12.4 grams, 0.10 mole) and 10 milliliters (ml) of pyridine were mixed together in 200 ml dichloromethane in a reaction flask. 9.1 ml (0.10 mole) of cyclopropane carboxylic acid chloride was added to the reaction mixture over a period of 2 minutes. The reaction was exothermic and temperature rose to 34° C. The reaction was allowed to stand for one hour at room temperature, after which the reaction mixture was washed with 200 ml of 5% sodium hydroxide and 100 ml of water. The resulting organic phase was separated and dried over anhydrous magnesium sulfate. Crystals formed, so that mixture was filtered and washed with 300 ml of acetone and the filtrate evaporated in vacuo to give a solid that was triturated with hexane to yield 16.7 grams, after drying. The product was identified by IR and NMR as the title compound, having a melting point of 130°-131° C. This compound will be referred to as Compound 1.

1. customrose to 34° C
2. washafter which the reaction mixture was washed with 200 ml of 5% sodium hydroxide and 100 ml of water
3. customThe resulting organic phase was separated
4. dry with materialdried over anhydrous magnesium sulfate
5. customCrystals formed, so that mixture
6. filtrationwas filtered
7. washwashed with 300 ml of acetone
8. customthe filtrate evaporated in vacuo
9. customto give a solid
10. customthat was triturated with hexane
11. customto yield 16.7 grams
12. customafter drying

ORD record

ord-91e1ae095e6847ed9e795538bec5aca4

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808600