Triethylamine → 7-Methanesulfonylmethyl-4-chloroquinoline

HRID 965001Notes

Reaction equation

HRID 965001 reaction equation
O[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(=O)=O.CC(C)=O.C(OCC)(=O)C>[CH3:21][S:22]([CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1)(=[O:24])=[O:23]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22054610(4-Chloroquinolin-7-yl)methanol

Product 1

HCID 190751107-Methanesulfonylmethyl-4-chloroquinoline

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 18522661Acetone cardiceSolvent

Procedure

7-Hydroxymethyl-4-chloroquinoline (930 mg, 4.82 mmol) dissolved in anhydrous methylene chloride (40 ml) was added with triethylamine (679 mg, 6.72 mmol). The mixture was cooled in dry ice/acetone bath, added dropwise with methanesulfonyl chloride (770 mg, 6.7 mmol) and the reactant was stirred for 20 minutes without the cooling bath. Then, the reactant was added under ice-water cooling with cool aqueous solution of saturated sodium bicarbonate (40 ml) and ethyl acetate (150 ml) and shaken to separate the organic layer. The separated organic layer was washed with saturated saline solution and dried over magnesium sulfate. The solvent was removed to obtain 7-methanesulfonylmethyl-4-chloroquinoline as oily product.

Workup

  1. stirringshaken
  2. customto separate the organic layer
  3. washThe separated organic layer was washed with saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-dd8a4311f2744953aaa33480d6579f42
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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