Sodium Hydroxide → 8-Chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

HRID 2051324Notes

Reaction equation

HRID 2051324 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:22]=[CH:21][C:11]2[C:12]3[CH2:13][CH2:14][C:15](=O)[NH:16][C:17]=3[CH2:18][CH2:19][C:10]=2[CH:9]=1.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:22]=[CH:21][C:11]2[C:12]3[CH2:13][CH2:14][CH2:15][NH:16][C:17]=3[CH2:18][CH2:19][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 104665398-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 198331348-Chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

147 g (1.94 mol) of lithium aluminum hydride are suspended in 4 l of tetrahydrofuran under argon. 454 g (1.94 mol) of 8-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin -3(2H)-one are slowly added thereto and the mixture is boiled under reflux for 2.5 hours. The mixture is then cooled and 470 ml of 18 percent sodium hydroxide solution are added thereto. The resulting mixture is stirred at room temperature for 30 minutes filtered and the filter residue is washed with tetrahydrofuran. Upon evaporation of the filtrate, there is obtained 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline as a yellow oil.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperatureThe mixture is then cooled
  3. filtrationfiltered
  4. washthe filter residue is washed with tetrahydrofuran
  5. customUpon evaporation of the filtrate

Sources & evidence

ORD record
ord-9fc0099a717c4ffc8d4e6930f3623173
Source dataset
uspto-grants-1991_05
Patent number
US05017608

Reaction notes

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