Triethylamine → 4-(Chloromethyl)-6-methoxy-quinoline

HRID 899966Notes

Reaction equation

HRID 899966 reaction equation
C(N(CC)CC)C.CS([Cl:12])(=O)=O.O[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1>ClCCl>[Cl:12][CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3385004-Hydroxymethyl-6-methoxyquinoline

Product 1

HCID 179006174-(Chloromethyl)-6-methoxy-quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.16 ml of triethylamine and 0.64 ml of methanesulfonyl chloride are successively added to a solution of 1.2 g of 4-hydroxymethyl-6-methoxyquinoline in 45 ml of dichloromethane, under an inert atmosphere of argon at a temperature in the region of 20° C. Stirring is maintained at this temperature for 3 hours. The reaction medium is concentrated under reduced pressure to give a brown residue. The product is used without further purification in the following step.

Workup

  1. temperatureis maintained at this temperature for 3 hours
  2. concentrationThe reaction medium is concentrated under reduced pressure
  3. customto give a brown residue
  4. customThe product is used without further purification in the following step

Sources & evidence

ORD record
ord-a487fe5f261f4611a7f4ef14eca8da73
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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