Thionyl Chloride → 3-(Chloromethyl)-8-methyl-2-o-tolylquinoline

HRID 2044820Notes

Reaction equation

HRID 2044820 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[C:8]([CH2:19]O)=[CH:7]2.O=S(Cl)[Cl:23]>C(Cl)(Cl)Cl>[Cl:23][CH2:19][C:8]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57707986(8-Methyl-2-o-tolylquinolin-3-yl)methanol

Product 1

HCID 575561733-(Chloromethyl)-8-methyl-2-o-tolylquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to Procedure C using (8-methyl-2-o-tolylquinolin-3-yl)-methanol (670 mg, 2.5 mmol) and SOCl2 (0.91 mL, 5 eq) in CHCl3 (10 mL). After isolation, the resultant oil was carried on crude without purification for the next step.

Workup

  1. customPrepared
  2. customAfter isolation, the resultant oil was carried on crude without purification for the next step

Sources & evidence

ORD record
ord-831fbfa52cc64820a9429ecfb1388637
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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