Methanesulfonyl chloride → 8-Chloro-5,6,7,8-tetrahydroquinoline

HRID 1194696Notes

Reaction equation

HRID 1194696 reaction equation
CS([Cl:5])(=O)=O.[N+:6]1([O-])[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>>[Cl:5][CH:14]1[C:15]2[N:6]=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate2×HCID 27781345,6,7,8-Tetrahydro-1-quinoliniumolate

Product 1

HCID 137121808-Chloro-5,6,7,8-tetrahydroquinoline

Conditions

Temperature
20 °C

Procedure

At ambient temprature, 3 ml of methane sulfonyl chloride were added slowly to 1.49 g of 5,6,7,8-tetrahydroquinoline-N-oxide with stirring under an inert atmosphere. The mixture was heated for 4 hours at 80° to 82° C., then cooled to 20° C. and poured into 20 ml of a saturated solution of sodium bicarbonate. Then, sodium bicarbonate was added until an alkaline pH was obtained and after extracting with methylene chloride, washing with water, drying the re-united organic solutions and distilling to dryness under reduced pressure, 1.53 g of 8-chloro-5,6,7,8-tetrahydroquinoline were obtained in the form of an oil.

Workup

  1. temperatureThe mixture was heated for 4 hours at 80° to 82° C.
  2. customwas obtained
  3. extractionafter extracting with methylene chloride
  4. washwashing with water
  5. customdrying the re-united organic solutions
  6. distillationdistilling to dryness under reduced pressure

Sources & evidence

ORD record
ord-152956ea72764899948f07a80548762b
Source dataset
uspto-grants-1989_03
Patent number
US04816465

Reaction notes

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