Triethylamine → 4-Quinolinylmethyl methanesulfonate

HRID 1198877Notes

Reaction equation

HRID 1198877 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 804794-(Hydroxymethyl)quinoline

Product 1

HCID 135408214-Quinolinylmethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (4.84 ml) in 20 ml of methylene chloride is slowly added over 20 minutes to a solution of 8.29 g of 4-hydroxymethylquinoline and 11 ml of triethylamine in 200 ml of methylene chloride at 0°. After completion of the reaction at room temperature, the reaction mixture is partitioned between methylene chloride and saturated potassium carbonate solution. The organic layer is dried over sodium sulfate and evaporated to dryness to yield 4-(methanesulfonyloxymethyl)quinoline as an oil.

Workup

  1. customAfter completion of the reaction at room temperature
  2. customthe reaction mixture is partitioned between methylene chloride and saturated potassium carbonate solution
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-9d71cf4b7b0244e5b9af3d67670fe156
Source dataset
uspto-grants-1990_02
Patent number
US04898854

Reaction notes

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