Thionyl Chloride → 8-Chloro-3-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

HRID 1730008Notes

Reaction equation

HRID 1730008 reaction equation
O[CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.S(Cl)([Cl:15])=O>>[ClH:15].[Cl:15][CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 123582223-Methyl-5,6,7,8-tetrahydroquinolin-8-ol

Product 1

HCID 214117248-Chloro-3-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

Conditions

Temperature
0 °C

Procedure

The 8-hydroxy product of Example 1 (15 g.) was added portionwise to thionyl chloride (33 g.) at 0° C and the mixture stirred at 0° C for 1 hour and heated at reflux for an additional 2 hours. The solvent was removed in vacuo and the residual oil heated at reflux for 1 hour with ethanol (15 ml.) to remove excess thionyl chloride. The resultant precipitate was recrystallised from ethanol-ether to give 8-chloro-3-methyl-5,6,7,8-tetrahydroquinoline hydrochloride as colourless needles (17.4 g.) m p. 177° C. (Found: C, 55.3; H, 6.1; N, 6.5 C10H12C1N.HC1 requires: C,55.1; H,6.0; N, 6.4%).

Workup

  1. temperatureheated
  2. temperatureat reflux for an additional 2 hours
  3. customThe solvent was removed in vacuo
  4. temperaturethe residual oil heated
  5. temperatureat reflux for 1 hour with ethanol (15 ml.)
  6. customto remove excess thionyl chloride
  7. customThe resultant precipitate was recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-40cf8a107a9442c086fede7473eff276
Source dataset
uspto-grants-1976_11
Patent number
US03991065

Reaction notes

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