2-Cyanomethyl-6-methoxy-1-tetralone → HCID 12832408, compound

HRID 46511Notes

Reaction equation

HRID 46511 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[C:5]1=O)#[N:2].[H][H]>C(O)C.[Ni]>[CH3:15][O:14][C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[CH:4]([CH2:3][CH2:1][N:2]=3)[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

5

Reactant 2

HCID 128324072-Cyanomethyl-6-methoxy-1-tetraloneHCID 178418361HCID 178418361, compound

Product 1

HCID 12832408HCID 12832408, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The solution of 50 g of 2-cyanomethyl-6-methoxy-1-tetralone in 1000 ml of ethanol is hydrogenated in the presence of 15 g of Raney nickel at atmospheric pressure and room temperature until 2 mole equivalents of hydrogen are consumed. The mixture is filtered, the filtrate evaporated and the crude product dissolved in 500 ml of N hydrochloric acid. The solution is washed with diethyl ether, treated with charcoal, filtered and the filtrate is basified with 3 N aqueous sodium hydroxide. It is extracted with methylene chloride, the extract dried, evaporated, the residue crystallized from petroleum ether and recrystallized from hexane, to yield the 7-methoxy-3,3a,4,5-tetrahydro-2H-benz[g]indole melting at 102°-104°.

Workup

  1. customare consumed
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated
  4. dissolutionthe crude product dissolved in 500 ml of N hydrochloric acid
  5. washThe solution is washed with diethyl ether
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. extractionIt is extracted with methylene chloride
  9. customthe extract dried
  10. customevaporated
  11. customthe residue crystallized from petroleum ether
  12. customrecrystallized from hexane

Sources & evidence

ORD record
ord-0807c7593680411f946d5c35a4e930f9
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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