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

HRID 2366851Notes

Reaction equation

HRID 2366851 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[C@H:7]([NH:15]C=O)[CH2:6][C@@H:5]1[CH3:18])(=[O:3])[CH3:2].Cl.[OH-].[Na+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[C@H:7]([NH2:15])[CH2:6][C@@H:5]1[CH3:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86669233HCID 86669233, compound

Product 1

HCID 67194540cis-1-Acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinamineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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

Workup

  1. temperatureat reflux for 3 hours
  2. customThe MeOH was evaporated under reduced pressure
  3. extractionthe organic material extracted with EtOAc (250 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-34f5ed545c35412480c9c21f18aa72b9
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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