Sodium Hydroxide → HCID 19833182, compound

HRID 1639368Notes

Reaction equation

HRID 1639368 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]3[CH2:9][CH2:10][C:11](=O)[NH:12][C:13]=3[CH2:14][CH2:15][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:7]2[C:8]3[CH2:9][CH2:10][CH2:11][NH:12][C:13]=3[CH2:14][CH2:15][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19791560HCID 19791560, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19833182HCID 19833182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.0 g of 10-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one are added portionwise within 35 minutes at 20° to 25° to a stirred suspension of 6.49 g of lithium aluminum hydride in 240 ml of dry tetrahydrofuran. The reaction mixture is subsequently boiled under reflux for 150 minutes. The mixture is cooled, treated at 0° to 10° with 21.0 ml of 6.5N sodium hydroxide solution, filtered and rinsed several times with 20 ml of tetrahydrofuran each time. Distillation of the solvent in a vacuum gives 10-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline which is processed directly.

Workup

  1. temperatureunder reflux for 150 minutes
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. washrinsed several times with 20 ml of tetrahydrofuran each time
  5. distillationDistillation of the solvent in a vacuum

Sources & evidence

ORD record
ord-cbdd91a9e9b84218a9de1f96a5c01fa5
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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