Hydrochloric Acid → HCID 59441893, compound

Participants

Reaction Steps

To a solution of 5-(methyloxy)-1-[3-(4-morpholinyl)propanoyl]-6-nitro-2,3-dihydro-1H-indole (0.44 g, 1.31 mmols) in absolute ethanol (150 mL) and DMA (20 mL) was added tin(II)chloride dihydrate (1.77 g, 7.84 mmols) and 1M HCl (3.0 mL). After overnight stirring, reaction was quenched with excess saturated Na HCO3 solution, stirred for one hr. and filtered through celite which was rinsed with methanol. After organic solvent removal, the aqueous layer was extracted with dichloromethane (2×200 mL), the organic layers were combined, adsorbed to silica gel and purified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH) to afford 5-(methyloxy)-1-[3-(4-morpholinyl)propanoyl]-2,3-dihydro-1H-indol-6-amine. ESIMS (M+H)+=306.

Provenance & Evidence