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

HRID 1397656Notes

Reaction equation

HRID 1397656 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-631809602ecd4c808196be32181ff67e
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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