Acetic Acid → 3-Chloro-N2-methyl-2,5-pyridinediamine

Temperature

60 °C

A suspension of 329 mg of 3-chloro-N-methyl-5-nitropyridin-2-ylamine, 489 mg of iron powder, and 9 ml of acetic acid was stirred at 60° C. for 2 hours. After the reaction solution was cooled to room temperature, ethanol was added thereto and the solution was filtrated through celite. The filtrate was concentrated under reduced pressure and ethyl acetate and a saturated aqueous sodium bicarbonate solution were added thereto. To the organic layer obtained by an operation of separation was added a 1M aqueous sodium hydroxide solution, followed by an operation of separation. The resulting organic layer was dried over anhydrous sodium sulfate and filtrated and then the resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol) to obtain 193 mg of 3-chloro-2-methylamino-5-aminopyridine as a brown oil.

1. temperatureAfter the reaction solution was cooled to room temperature
2. filtrationthe solution was filtrated through celite
3. concentrationThe filtrate was concentrated under reduced pressure and ethyl acetate
4. additiona saturated aqueous sodium bicarbonate solution were added
5. customTo the organic layer obtained by an operation of separation
6. customfollowed by an operation of separation
7. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
8. filtrationfiltrated
9. concentrationthe resulting filtrate was concentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (chloroform:methanol)

ORD record

ord-ca9e05e0f0704646ab0f4067f4674cf3

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585878B2