Ethanol → Benzeneacetic acid, 2,4-dinitro-, ethyl ester
Reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=[O:15])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:22][CH2:23]O>>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([O:16][CH2:22][CH3:23])=[O:15])([O-:3])=[O:2]Participants
4
Procedure
A mixture of 2,4-dinitrophenylacetic acid (10 g) and H2SO4 (0.1 eq) in EtOH (300 ml) was refluxed overnight. The solvent was evaporated, and EtOAc (150 ml) and H2O (200 ml) were added. The solution was extracted three times with EtOAc and washed with H2O followed by brine, dried over Na2SO4 and evaporated to give ethyl 2-(2,4-dinitrophenyl)acetate for next step without further purification. The above compound (5 g) was mixed with Pd—C (10%, 500 mg) in EtOH (200 ml) and hydrogenated under H2 atmosphere overnight. The reaction was filtered through Celite and evaporated. The residue was washed with EtOAc and filtered to give 6-aminoindolin-2-one.