Dimethyl Sulfoxide → HCID 21393834, compound

HRID 461501Notes

Reaction equation

HRID 461501 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].O.[CH3:16]S(C)=O>>[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 962Water2×HCID 24758Sodium hydrideHCID 125950627,8-Dichloroisoquinoline

Product 1

HCID 21393834HCID 21393834, compound

Conditions

Temperature
70 °C

Procedure

Alternatively, 7,8-dichloro-1-methylisoquinoline is prepared by the following procedure. 7,8-Dichloroisoquinoline (0.019 mole) in 100 ml. of dimethylsulfoxide is added to a solution of sodium hydride (0.11 mole) in 100 ml of dimethylsulfoxide at 70° C. The reaction mixture is stirred at 70° C. for four hours under a nitrogen atmosphere. The reaction mixture is cooled, 100 ml. of water is added, and the mixture is poured into 1500 ml. of water. The aqueous mixture is extracted with benzene. The extract is washed, dried over sodium sulfate and evaporated to give 7,8-dichloro-1-methylisoquinoline.

Workup

  1. customAlternatively, 7,8-dichloro-1-methylisoquinoline is prepared by the following procedure
  2. temperatureThe reaction mixture is cooled
  3. additionthe mixture is poured into 1500 ml
  4. extractionThe aqueous mixture is extracted with benzene
  5. washThe extract is washed
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-53383e55b9544eaba84b3df80e117137
Source dataset
uspto-grants-1977_12
Patent number
US04062961

Reaction notes

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