5-Amino-2-chloropyridine → 6-chloro-N-methylpyridin-3-amine

To 5.0 g (0.039 mole) of 5-amino-2-chloropyridine was added 40 ml of ethyl orthoformate and the mixture was refluxed for 5 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in 50 ml of EtOH. After addition of 1.8 g of sodium borohydride, the mixture was stirred at 70°-80° C. for 3 hours. The reaction mixture was concentrated and after addition of 50 ml of iced water and 5 ml of concentrated hydrochloric acid, the mixture was adjusted to pH 7-8 with NaHCO3 and extracted with AcOEt (50 ml×3). The AcOEt layers were pooled, washed with water and dried over MgSO4. The AcOEt was distilled off and hexane was added to the crystalline residue. The crystals are collected by filtration, washed with hexane and dried to give 5.1 g of the title compound as white crystals.

1. temperaturethe mixture was refluxed for 5 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. dissolutionthe residue was dissolved in 50 ml of EtOH
4. additionAfter addition of 1.8 g of sodium borohydride
5. concentrationThe reaction mixture was concentrated
6. additionafter addition of 50 ml of iced water and 5 ml of concentrated hydrochloric acid
7. extractionextracted with AcOEt (50 ml×3)
8. washwashed with water
9. dry with materialdried over MgSO4
10. distillationThe AcOEt was distilled off
11. additionhexane was added to the crystalline residue
12. filtrationThe crystals are collected by filtration
13. washwashed with hexane
14. customdried

ORD record

ord-cec17f52a9194855a0df19f7565ace91

Source dataset

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05175301