Formic Acid → N-(4-chloroquinolin-3-yl)formamide

Acetic anhydride (16 mL, 170 mmol) was cooled to 0° C., and formic acid (7.2 mL of 97% pure material, 190 mmol) was added over a period of ten minutes. The solution was stirred for 2.5 hours at room temperature and then added to a stirred solution of 3-amino-4-chloroquinoline (10.0 g, 56.0 mmol) in tetrahydrofuran (THF) (100 mL). The reaction was stirred for one hour at room temperature and then concentrated under reduced pressure. Methanol (50 mL) was added to the residue, stirred for 30 minutes, and removed under reduced pressure. The residue was then stirred with dichloromethane (150 mL) and saturated aqueous sodium bicarbonate (50 mL) for three days. A solid was present and was isolated by filtration and dried under high vacuum. The filtrate was concentrated under reduced pressure, and the residue was dissolved in methanol (400 mL). The solution was dried over potassium carbonate, filtered, and concentrated under reduced pressure. The residue was combined with the solid isolated by filtration to provide 9.6 g of 4-chloroquinolin-3-ylformamide as a brown solid.

1. stirringThe reaction was stirred for one hour at room temperature
2. concentrationconcentrated under reduced pressure
3. additionMethanol (50 mL) was added to the residue
4. stirringstirred for 30 minutes
5. customremoved under reduced pressure
6. stirringThe residue was then stirred with dichloromethane (150 mL) and saturated aqueous sodium bicarbonate (50 mL) for three days
7. customwas isolated by filtration
8. customdried under high vacuum
9. concentrationThe filtrate was concentrated under reduced pressure
10. dissolutionthe residue was dissolved in methanol (400 mL)
11. dry with materialThe solution was dried over potassium carbonate
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customisolated by filtration

ORD record

ord-e5f7a6689c9a428da3b642f3adc5ad19

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579359B2