Methanol → HCID 19829819, compound

A mixture of 3-bromoaniline (88.6 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). The resulting solid was filtered off, dissolved in dichloromethane (1000 ml), and this solution was dried and evaporated to give a solid (94 g). A portion of this solid (1 g) was purified by FCC eluting with System A (1:1) to give a semi-solid which was recrystallised from System A to give the title compound, m.p. 66°-68°.

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. filtrationThe resulting solid was filtered off
8. dissolutiondissolved in dichloromethane (1000 ml)
9. customthis solution was dried
10. customevaporated

ORD record

ord-7d95aa1703fc4a0db9c17754cdc697c0

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05023255