[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([C:15]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6].[CH3:26]I.O>CCCCCC.C1COCC1>[CH3:3][O:4][C:5]([C:7]1[N:8]([CH3:26])[C:9]2[C:14]([C:15]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6]6.73 g (0.16 mole) of 57% sodium hydride in mineral oil was washed with hexane and suspended in 500 ml of THF. To this was added 43.4 g (0.139 mole) of methyl-3-[o-nitrophenoxy]-indole-2-carboxylate. The mixture was stirred at reflux for 1 hour, then 42.6 g (0.3 mole) of methyl iodide was added and reflux continued for 3 hours. Water (5 ml) was added, the THF removed by distillation and the gummy residue recrystallized from isopropanol to give analytical material as yellow needles, mp. 119°-21°.
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