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

HRID 569649Notes

Reaction equation

HRID 569649 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 were 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 were slowly added thereto and the mixture was boiled under reflux for 2.5 hours. The mixture was then cooled, 470 ml of 18 percent sodium hydroxide solution were added thereto, the resulting mixture was stirred at room temperature for 30 minutes, filtered and the filter residue was washed with tetrahydrofuran. Upon evaporation of the filtrate there was 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 was then cooled
  3. filtrationfiltered
  4. washthe filter residue was washed with tetrahydrofuran
  5. customUpon evaporation of the filtrate there

Sources & evidence

ORD record
ord-6474cb477e644736a598c7433bc053b5
Source dataset
uspto-grants-1988_03
Patent number
US04732979

Reaction notes

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