Chloroform → 3-(Chloromethyl)-2-(3-fluorophenyl)-8-methoxyquinoline hydrochloride

HRID 216856Notes

Reaction equation

HRID 216856 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH2:18]O)=[CH:16][C:15]3[C:10](=[C:11]([O:20][CH3:21])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)(Cl)[Cl:23].S(Cl)([Cl:28])=O>>[ClH:23].[Cl:28][CH2:18][C:17]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[O:20][CH3:21]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 68945460(2-(3-Fluorophenyl)-8-methoxyquinolin-3-yl)methanol

Product 1

HCID 689445683-(Chloromethyl)-2-(3-fluorophenyl)-8-methoxyquinoline hydrochloride

Procedure

A solution of (2-(3-fluorophenyl)-8-methoxyquinolin-3-yl)methanol (2.2330 g, 7.882 mmol) in chloroform (26.27 mL, 7.882 mmol) was treated with thionyl chloride (2.868 mL, 39.41 mmol) dropwise, and the reaction mixture was stirred at room temperature. After 3 h, the mixture was concentrated under reduced pressure and co-evaporated three times with CH2Cl2 to give 3-(chloromethyl)-2-(3-fluorophenyl)-8-methoxyquinoline hydrochloride as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.59 (1H, s), 7.55-7.65 (3H, m), 7.44-7.52 (2H, m), 7.33-7.41 (1H, m), 7.23-7.30 (1H, m), 4.91 (2H, s); LC-MS (ESI) m/z 302.0 [M+H]+ (Exact Mass of neutral form: 301.067). The yellow solid was carried on crude without purification for the next step.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9508c1440a554731aecd349ee9d48103
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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