Water → 2-Amino-3-(3-chloropropyloxy)pyridine

To a suspension of 48.7 ml (200 mmol) of a 4.1M sodium methoxide solution in 100 ml of dimethyl sulfoxide, 22.03 g (200 mmol) of 2-amino-3-hydroxypyridine was added at room temperature, followed by stirring at 80° C. for 10 minutes to dissolve the latter. After the reaction mixture was cooled, the methanol was distilled off. To this mixture, 19.8 ml (200 mmol) of 1-bromo-3-chloropropane was added at 0° C., followed by stirring for 30 minutes. The reaction mixture was poured into water (400 ml), extracted with chloroform, washed with2N aqueous sodium hydroxide and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate). The obtained crude crystal was washed with diethyl ether-n-hexane to yield 20.48 g (54.8%, white powder) of the desired product.

1. additionwas added at room temperature
2. dissolutionto dissolve the latter
3. temperatureAfter the reaction mixture was cooled
4. distillationthe methanol was distilled off
5. stirringby stirring for 30 minutes
6. extractionextracted with chloroform
7. washwashed with2N aqueous sodium hydroxide
8. customdried
9. distillationafter which the solvent was distilled off
10. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate)
11. customThe obtained crude crystal
12. washwas washed with diethyl ether-n-hexane

ORD record

ord-578395d6d870492fbb9c516150464d45

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05840732