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

HRID 2044932Notes

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

Reactant 3

HCID 6212Chloroform

HCID 24386Thionyl Chloride

HCID 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 (1 H, s), 7.55-7.65 (3 H, m), 7.44-7.52 (2 H, m), 7.33-7.41 (1 H, m), 7.23-7.30 (1 H, m), 4.91 (2 H, s); LC-MS (ESI) m/z 302.0 [M+H]+ (Exact Mass of neutal form: 301.067). The yellow solid was carried on crude without purification for the next step.

Workup

concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-226ac97a265c43b884056eb80259b397
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586739B2

Reaction notes

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