Triethylamine → 4-Quinolinylmethyl methanesulfonate

HRID 345319Notes

Reaction equation

HRID 345319 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-e4e7426ef6fa41e792a4f1e4567005dd
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

Loading…