Potassium Hydroxide → HCID 18706872, compound

HRID 1421889Notes

Reaction equation

HRID 1421889 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].COCCO[AlH2-]OCCOC.[Na+].[CH3:27][O:28][C:29]1[C:42]2[CH2:41][CH2:40][C:39]3[N:38]([CH3:43])[C:37](=O)[CH2:36][CH2:35][C:34]=3[C:33]=2[CH:32]=[CH:31][CH:30]=1.[OH-].[K+]>C1(C)C=CC=CC=1.O>[CH3:27][O:28][C:29]1[C:42]2[CH2:41][CH2:40][C:39]3[N:38]([CH3:43])[CH2:37][CH2:36][CH2:35][C:34]=3[C:33]=2[CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 16684438Red-AlHCID 18706890HCID 18706890, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 18706872HCID 18706872, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of sodium bis-(2-methoxyethoxy)aluminium hydride in toluene (Red-Al, 65% wt, 37.2 ml, 124 mmol) was added to a stirred solution of 7-methoxy-4-methyl-1,4,5,6-tetrahydro-2H-benzo[f]quinoline-3-one (10 g, 41.2 mmol) in toluene (200 ml). The mixture was heated at reflux, under argon for 6 h and allowed to cool. Water (7 ml) was added dropwise with ice cooling and the aluminium salts dissolved by addition of 50% KOH (37 ml). The organic phase was separated, washed with water (2×100 ml), dried (Na2SO4) and concentrated in vacuo to afford an oil which was chromatographed on silica gel, with 10-15% ethyl acetate-pentane gradient elution to give the title compound as a yellow oil (5.5 g, 58%)

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux, under argon for 6 h
  3. temperatureto cool
  4. customThe organic phase was separated
  5. washwashed with water (2×100 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto afford an oil which
  9. customwas chromatographed on silica gel, with 10-15% ethyl acetate-pentane gradient elution

Sources & evidence

ORD record
ord-06583c34a9af48cca47dd515b279d787
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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