반응 #61586

반응 방정식

hydrazine hydrate

compound 28

1,5-Dihydro-3-phenyl-[1,2]diazepino[4,5,6-cd]-indol-6-one

methyl indole-4-carboxylate

acetyl chloride

aluminum chloride

→

1,5-dihydro-3-methyl-[1,2]diazepino[4,5,6-cd]-indol-6-one

용매

MeOH

HCl

dichloroethane

반응 조건

후처리

1. 1
   기타The product precipitated
2. 2
   여과was collected by filtration
3. 3
   세척rinsed with ice-cold MeOH

실험 절차

In a manner similar to that described for compound 28, a solution of methyl indole-4-carboxylate (427 mg, 2.44 mmol) in dichloroethane (7 mL) was treated with acetyl chloride (0.5 mL) and aluminum chloride (130 mg). The intermediate ketone (198 mg, 0.92 mmol) in MeOH (5 mL) and conc. HCl (0.05 mL) was treated, as described, with hydrazine hydrate (0.1 mL). The product precipitated, was collected by filtration and rinsed with ice-cold MeOH to give 1,5-dihydro-3-methyl-[1,2]diazepino[4,5,6-cd]-indol-6-one, 168 mg (92%) as a bright yellow solid: m.p. 335-336° C.; 1H NMR (300 MHz, d6-DMSO) δ 2.17 (s, 3H), 7.19 (t, J=7.8 Hz, 1H), 7.54 (m, 2H), 7.67 (d, J=2.8 Hz, 1H), 10.12 (s, 1H), 11.90 (br s, 1H). HRMS (FAB, MH+) Calcd for C11H10N3O: 200.0824. Found: 200.0827. Anal. (C11H9N3O) C, H, N.

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