Ammonium formate → Ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate

反応式

C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12]2

参加物

実験手順

A mixture of crude ethyl 5-(benzyloxy)-1-methyl-1H-indole-2-carboxylate (1.07 g, 3.46 mmol), 10% palladium on carbon (500 mg, 0.47 mmol) and ammonium formate (1.09 g, 17.29 mmol) in 50 mL ethanol was sparged with argon three times and heated at reflux for 1 h. The mixture was cooled, diluted with 100 mL ethanol and filtered through Celite, washed with ethanol and concentrated to give ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate (1.82 g, 49% over two steps).