Acetic Acid → HCID 13424431, compound

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)(=O)C>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=1

Participants

Procedure

A mixture of 6 g of ethyl 2-(4-benzyloxyphenylamino)-5-methoxybenzoate, 30 ml of acetic acid, 270 ml of ethanol and 500 mg of 10% palladium-on-carbon catalyst was hydrogenated on a Parr apparatus for eight hours. The mixture was filtered, the filtrate stripped of solvent and the residue partitioned between ether and saturated sodium bicarbonate solution. The ether solution was dried over anhydrous magnesium sulfate and the solvent removed to give 5.6 g of ethyl 2-(4-hydroxyphenylamino)-5-methoxybenzoate as a yellow solid, m.p. 134°-136° C. when recrystallized from toluene.