Methanol → trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl chloride

HRID 1198540

Reaction equation

HRID 1198540 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[CH2:21]O)=[N:13]2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+].CO>ClCCCl>[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[CH2:21][Cl:3])=[N:13]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 10827738trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl alcohol

Product 1

HCID 19369489trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Thionyl chloride (3.6 ml., 49.3 mmol) was added rapidly to a stirred solution of 3-[2(E)-(7-chloroquinolin-2-yl)ethenyl]benzyl alcohol (Example 6a part (ii)) (11.7 g, 39.5 mmol) in 1,2-dichloroethane (300 ml) at 50° C. giving an immediate yellow precipitate. The mixture was stirred for 1 hour and cooled to room temperature then the mixture was shaken with saturated sodium bicarbonate solution (400 ml) and methanol (50 ml) to give two clear phases. The aqueous phase was extracted with dichloromethane and the combined solvent phase was dried and evaporated.

Workup

  1. customgiving an immediate yellow precipitate
  2. customto give two clear phases
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. customthe combined solvent phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-9828fbef99d24a878dc0b78475db45fd
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Linked notes

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