HCID 20399854, compound → HCID 13472127, compound

HRID 1981138Notes

Reaction equation

HRID 1981138 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 20399854HCID 20399854, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13472127HCID 13472127, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of the above 1-(6-methoxyhexanoyl)-1,2,3,4-tetrahydroquinoline (2.7 g) in ether (200 ml) containing lithium aluminium hydride (9.9 g) was refluxed for 6 hours, then cooled and diluted with water. The ethereal solution was dried and evaporated and the residue was chromatographed on silica gel, eluting with 99:1 methylene chloride:methanol, so as to obtain the title compound as an oil.

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperaturecooled
  3. customThe ethereal solution was dried
  4. customevaporated
  5. customthe residue was chromatographed on silica gel
  6. washeluting with 99:1 methylene chloride

Sources & evidence

ORD record
ord-4804ac58c97c46da8fb4a00d440a0f11
Source dataset
uspto-grants-1985_04
Patent number
US04512990

Reaction notes

Loading…