Methanol → HCID 22669248, compound

A mixture of 3-methoxyaniline (61.6 g), methyl chloroacetate (44 ml), sodium acetate trihydrate (114 g) and methanol (70 ml) was heated under reflux for 18 h. The mixture was poured into water (500 ml) and extracted with dichloromethane (3×250 ml). The combined, dried organic extracts were evaporated and the residue was treated with 10% concentrated sulphuric acid in methanol (250 ml). After 3 h the solution was poured carefully into 8% sodium bicarbonate (1200 ml) and partitioned with ether (4×500 ml). The combined organic extracts were washed successively with 0.5M citric acid solution (5×200 ml) and brine (500 ml), dried and evaporated to give an oil. Purification by FCC eluting initially with ether:petroleum ether 60°-80° (2:3) and then with ether:petroleum ether 60°-80° (1:1) gave the title compound (52 g) as an oil, t.l.c. (System A, 1:1) Rf 0.31.

1. temperaturewas heated
2. temperatureunder reflux for 18 h
3. extractionextracted with dichloromethane (3×250 ml)
4. customdried organic extracts were evaporated
5. additionthe residue was treated with 10% concentrated sulphuric acid in methanol (250 ml)
6. additionAfter 3 h the solution was poured carefully into 8% sodium bicarbonate (1200 ml)
7. custompartitioned with ether (4×500 ml)
8. washThe combined organic extracts were washed successively with 0.5M citric acid solution (5×200 ml) and brine (500 ml)
9. customdried
10. customevaporated
11. customto give an oil
12. customPurification by FCC
13. washeluting initially with ether

ORD record

ord-1a0b6d17bae84d918dd41fdf7a5c9652

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04985427