Thionyl Chloride → HCID 57556185, compound

HRID 2074502Notes

Reaction equation

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

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 57556190HCID 57556190, compound

Product 1

HCID 57556185HCID 57556185, compoundYield 89%

Procedure

Prepared according to Procedure C using (2-(2-fluorophenyl)-8-methylquinolin-3-yl)methanol (0.700 g, 2.62 mmol) in SOCl2 (2 mL, 27.4 mmol, 10.5 eq). 3-(chloromethyl)-2-(2-fluorophenyl)-8-methyl-quinoline (0.665 g, 89%) was obtained after purification as a brown foam. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.61 (1 H, s), 7.92 (1 H, d, J=7.9 Hz), 7.71 (1 H, d, J=6.7 Hz), 7.53-7.66 (3H, m), 7.40 (2 H, t, J=7.9 Hz), 4.81 (2 H, s), 2.69 (3 H, s) Mass Spectrum (ESI) m/e=286.1 and 288.1 (M+1)

Workup

customPrepared

Sources & evidence

ORD record: ord-abe7f43b9e6442c6a55ea56e9715b86c
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919498B2

Reaction notes

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