Dimethyl Sulfoxide → HCID 21393834, compound

HRID 1288477Notes

Reaction equation

HRID 1288477 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.[CH3:13]S(C)=O.[H-].[Na+]>O>[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 21393834HCID 21393834, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

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 4 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. customat 70° C
  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-dd3e80d8e2844313aabb83c81a95059d
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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