Ethanol → Glycine, N-(m-nitrophenyl)-, ethyl ester
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:15](O)[CH3:16]>O>[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2 g of 3-nitrophenylglycine are heated for 20 hours with stirring at a temperature in the region of 100° C. in 100 cm3 of absolute ethanol containing 20 cm3 of 6.5N hydrochloric ethanol. The suspension is filtered at a temperature in the region of 50° C.; the filtrate is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained is taken up in water and then extracted with about 100 cm3 of ethyl acetate. The aqueous phase is made alkaline by addition of sodium carbonate until a pH in the region of 10 is obtained. The medium is extracted with ethyl acetate; the combined extracts are washed with aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure (5 kPa) at 40° C. 1 g of ethyl 3-nitrophenylglycinate is obtained in the form of a yellow oil. (Rf=0.38 in a 95/5 by volume mixture of dichloromethane/methanol, on a Merck 60F254R silica plate).