32818-79-4 → HCID 5249961, compound

HRID 325771Notes

Reaction equation

HRID 325771 reaction equation
CO[C:3]1[CH2:12][C:11]([O:13]C)=[C:10]2[CH:5]([CH2:6][CH2:7][N:8]([CH3:15])[CH2:9]2)[CH:4]=1.CN1CCC2C(C(=O)CC(=O)C2)C1.[CH3:29][CH2:30][C:31](/[C:33](/[CH3:36])=[N:34]/O)=O>C(O)(=O)C.[Zn]>[CH2:30]([C:31]1[C:12]2[C:11](=[O:13])[CH:10]3[CH:5]([CH2:6][CH2:7][N:8]([CH3:15])[CH2:9]3)[CH2:4][C:3]=2[NH:34][C:33]=1[CH3:36])[CH3:29]

Participants

6

Reactant 3

HCID 957678232818-79-4HCID 128559332-Methylhexahydroisoquinoline-6,8(2H,7H)-dioneHCID 12868345HCID 12868345, compound

Product 1

HCID 5249961HCID 5249961, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

1,2,3,4,4a,7-Hexahydro-6,8-dimethoxy-2-methylisoquinoline (0.56 g, 2.68 mmol) was heated to 90°-100° in 70% aqueous acetic acid (10 ml) to hydrolyze the bis(enolether) to the octahydro-2-methylisoquinolin-6,8-dione. To the hot solution was added zinc dust (0.6 g, 9.25 mmol) and 2-isonitroso-3-pentanone (0.7 g, 6.1 mmol). The mixture was refluxed for 3 hours, cooled and filtered to remove zinc and zinc acetate. The filtrate was concentrated to dryness on a rotary evaporator and the residue was dissolved in dichloromethane. To the solution was added ammonium hydroxide and the layers were separated. The organic layer was washed with brine and dried over anhydrous sodium sulfate and concentrated to give the crude product. Chromatography of the crude product on Alumina III afforded 3-ethyl-2,6-dimethyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinolin-4-one as a white solid (0.19 g, 29% yield).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove zinc and zinc acetate
  5. concentrationThe filtrate was concentrated to dryness on a rotary evaporator
  6. dissolutionthe residue was dissolved in dichloromethane
  7. additionTo the solution was added ammonium hydroxide
  8. customthe layers were separated
  9. washThe organic layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customto give the crude product

Sources & evidence

ORD record
ord-aca55829dabb410a91167dc6a9fce1cd
Source dataset
uspto-grants-1984_04
Patent number
US04442291

Reaction notes

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