Hydrochloric Acid → cis-1-Acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinamine

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Reaction Steps

To a suspension of [(cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide (for a preparation see Intermediate 43) (4 g, 12.9 mol) in MeOH (50 mL) was added 6N HCl (6.5 mL, 38.6 mmol). The resulting mixture was stirred at reflux for 3 hours and the medium was made basic by the addition of 2N NaOH. The MeOH was evaporated under reduced pressure and the organic material extracted with EtOAc (250 mL). The organic phase was washed with brine, dried over Na2SO4 and concentrated to dryness to afford the title compound as an oil (3.3 g, 91%); LC/MS (Method E) m/z 284 [M+H]+, Rt=2.18 min

Provenance & Evidence