Thionyl Chloride → HCID 23018027, compound

HRID 1788399Notes

Reaction equation

HRID 1788399 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2[CH2:17]O>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:17][C:11]1[C:10]2[C:15](=[C:6]([F:5])[CH:7]=[CH:8][CH:9]=2)[N:14]=[C:13]([CH3:16])[CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23017958HCID 23017958, compound

Product 1

HCID 23018027HCID 23018027, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

At 0° C., 0.75 mL (10.4 mmol) of thionyl chloride was dropped into a solution of 1.00 g (5.23 mmol) of (8-fluoro-2-methylquinolin-4-yl)methanol obtained in the above 1) in chloroform (12 mL) and stirred for 15 hours at room temperature. The reaction mixture was removed under a reduced pressure and then, the residue was washed with ethyl acetate to obtain 1.29 g (yield 100%) of 4-chloromethyl-8-fluoro-2-methylquinoline hydrochloride (XII-124). Its physical property is shown below.

Workup

  1. customThe reaction mixture was removed under a reduced pressure
  2. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-a4a0988fa12e4acb83ea520bc0e7ed4c
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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