Sodium Hydroxide → 4-Chloro-5,6,7,8-tetrahydroquinoline

HRID 1613589Notes

Reaction equation

HRID 1613589 reaction equation
[N+]([C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N+:7]([O-])=[CH:6][CH:5]=1)([O-])=O.P(Cl)(Cl)[Cl:16].[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:16][C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24387Phosphorus trichlorideHCID 148359604-Nitro-5,6,7,8-tetrahydroquinoline 1-oxide

Product 1

HCID 109428314-Chloro-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the crude product of Step 1 (36.5 g, 188 mmol) in chloroform (500 ml) was treated over 30 min with phosphorus trichloride (80 g, 580 mmol) at 0°, heated under reflux for 1 h, cooled to room temperature, and poured onto ice (2 Kg). The mixture was basified with sodium hydroxide and the layers separated. The aqueous phase was extracted with chloroform (500 ml).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. additionpoured onto ice (2 Kg)
  4. customthe layers separated
  5. extractionThe aqueous phase was extracted with chloroform (500 ml)

Sources & evidence

ORD record
ord-267ea5c7d4fd4d5fa78c194b1352f537
Source dataset
uspto-grants-1993_03
Patent number
US05194439

Reaction notes

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