Methanol → HCID 54396632, compound

A solution of sodium nitrite (30 g) in water (200 ml) was added dropwise to a solution of N-(3-bromophenyl)glycine methyl ester (94 g) in aqueous acetic acid (850 ml) at 0°. After 1 h, methanol (200 ml) was added and the mixture was cooled to -10°. Zinc dust (351 g) was added portionwise over 2 h during which time the temperature was maintained at -10° to 0°. The mixture was then allowed to warm to room temperature, poured into ethyl acetate (1000 ml) and filtered. The filtrate was poured into water (1000 ml) and the layers were separated. The organic extract was washed with 2N sodium carbonate solution (500 ml) and solid sodium carbonate was added until the solution was basic. The aqueous extract was re-extracted using ethyl acetate (1000 ml) and the combined organic extracts were dried and evaporated. The residue was purified by FCC eluting with System A (1:1) to give the title compound (25.1 g) as an oil, t.l.c. (System A, 1:1) Rf 0.26.

1. temperaturethe mixture was cooled to -10°
2. temperaturewas maintained at -10° to 0°
3. filtrationfiltered
4. additionThe filtrate was poured into water (1000 ml)
5. customthe layers were separated
6. extractionThe organic extract
7. washwas washed with 2N sodium carbonate solution (500 ml) and solid sodium carbonate
8. additionwas added until the solution
9. extractionThe aqueous extract
10. extractionwas re-extracted
11. customthe combined organic extracts were dried
12. customevaporated
13. customThe residue was purified by FCC
14. washeluting with System A (1:1)

ORD record

ord-9306733dbfd140f6ac004e74189d46f0

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05023255