Hydrochloric Acid → 6H-Benzo[b]quinolizin-6-one, 1,2,3,4,11,11a-hexahydro-

HRID 583255Notes

Reaction equation

HRID 583255 reaction equation
[CH2:1]1[C:10]2[N:5]([C:6](=[O:15])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl>C(O)C.[Pd]>[CH2:1]1[CH:10]2[N:5]([C:6](=[O:15])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12730636HCID 12730636, compound

Product 1

HCID 27527926H-Benzo[b]quinolizin-6-one, 1,2,3,4,11,11a-hexahydro-Yield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1,3,4,6-tetrahydro-2H-benzo[b]quinolizin-6-one (4.02 g, 20.2 mmol) (M. A. Haimova, V. I. Ognyanov, and N. M. Mollov, Synthesis, 1980, 845) in ethanol (250 ml) and 2.5M hydrochloric acid (10 ml) was added 10% palladium-on-carbon (0.8 g) and the solution was shaken on a Parr Hydrogenator for 72 h. The catalyst was filtered off and the filtrate was concentrated to give an oil which was partitioned between ethyl acetate and dilute base. The dried (magnesium sulfate) organic phase was concentrated in vacuo and then placed on a high vacuum system to give the title compound as a white solid (3.8 g, 94%), m.p. 88-92° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customto give an oil which
  4. customwas partitioned between ethyl acetate
  5. additiondilute base
  6. dry with materialThe dried (magnesium sulfate) organic phase
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-af9282bc18b04270b5bced1947c83fce
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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