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

HRID 216743Notes

Reaction equation

HRID 216743 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-d6276ba642af47418dcbba960a738f46
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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