Thionyl Chloride → 8-Chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline

HRID 216747Notes

Reaction equation

HRID 216747 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH2:18]O)=[CH:16][C:15]2[C:10](=[C:11]([Cl:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1.O=S(Cl)[Cl:23]>>[Cl:20][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[N:9]=[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:17]([CH2:18][Cl:23])=[CH:16]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 57707777(2-(2-Chlorophenyl)-8-chloroquinolin-3-yl)methanol

Product 1

HCID 592646338-Chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline

Procedure

Prepared according to Procedure C using (2-(2-chlorophenyl)-8-chloroquinolin-3-yl)methanol (0.675 g, 2.22 mmol) and SOCl2 (0.81 mL). 8-Chloro-3-(chloro-methyl)-2-(2-chlorophenyl)quinoline was obtained as a yellow foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.53 (1H, s), 7.88 (1H, dd, J=8.2, 1.2 Hz), 7.81 (1H, dd, J=7.4, 1.2 Hz), 7.48 (1H, d, J=7.4 Hz), 7.42-7.46 (1H, m), 7.27-7.41 (3H, m), 4.63 (1H, d, J=9.8 Hz), 4.33-4.45 (1H, m) Mass Spectrum (ESI) m/e=322.0 and 324.0 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-fe336001edc34c62b2cb8f6770d24201
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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