HCID 22120793, compound → HCID 54252789, compound

Participants

Reaction Steps

N-(3-Phenoxyphenyl)glycine methyl ester (Intermediate 48; 10 g, 0.0389 mol) was dissolved in a mixture of glacial acetic acid (60 ml) and water (7 ml) and the solution was cooled to between 0° and 5° C. A solution of sodium nitrite (2.8 g, 0.0408 mol) in water (8.5 ml) was added to this over 15 min at the same low temperature. The solution was stirred for 1 h before being cooled to between 0° and -10° C. Zinc powder (9.9 g, 0.1517 mol) was gradually added at this temperature and the reaction was then stirred at 0° to 5° C. for 4 h. It was then poured into water (300 ml) and extracted with ethyl acetate (3×150 ml). The organic extract was washed with 8% sodium bicarbonate solution until effervescence had ceased. It was then dried and evaporated to give a dark brown oil. This was purified by FCC on deactivated silica (200 g) eluting with hexane-chloroform (2:1) to give the title compound as a brown oil (2.7 g, 25%).

Provenance & Evidence