6-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one → 6-Bromo-1,2,3,4-tetrahydro-4,4-dimethylquinoline

HRID 2254091Notes

Reaction equation

HRID 2254091 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:20])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[NH:11][C:10](=O)[CH2:9]1>C1COCC1.C(OCC)C>[CH3:7][C:8]1([CH3:20])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[NH:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 107295896-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 108239326-Bromo-1,2,3,4-tetrahydro-4,4-dimethylquinoline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 23.5 ml of 1.0M (23.5 mmol) lithium aluminum hydride in THF, heated to reflux under nitrogen, was added a solution of 4.95 g (19.48 mmol) of 4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline in 50 ml of dry THF and 100 ml of dry diethyl ether via a double-ended needle. The mixture was heated at reflux for 2 hours and then cooled to room temperature. The reaction mixture was then quenched by the slow addition of 25 ml of water followed by 50 ml of 5% NaOH solution. The mixture was extracted with 2×25 ml of ether, the organic extracts were combined and washed successively with 25 ml each of water and saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 15% ethyl acetate in hexanes) to give the title compound as a brown oil.

Workup

  1. temperatureto reflux under nitrogen
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 2 hours
  4. customThe reaction mixture was then quenched by the slow addition of 25 ml of water
  5. extractionThe mixture was extracted with 2×25 ml of ether
  6. washwashed successively with 25 ml each of water and saturated NaCl solution
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customthe residue purified by flash chromatography (silica; 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d8107adeb26547ad9935e29bd9fd25dc
Source dataset
uspto-grants-1993_08
Patent number
US05234926

Reaction notes

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