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

HRID 1639357Notes

Reaction equation

HRID 1639357 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-4376940c6975428b81b56d399235fbb7
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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