Chloroform → HCID 86630637, compound

HRID 1397758Notes

Reaction equation

HRID 1397758 reaction equation
[Cl: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[O:18][C:19]([F:22])([F:21])[F:20])[C:8]([CH2:23]O)=[CH:7]2.C(Cl)(Cl)[Cl:26].S(Cl)(Cl)=O>>[ClH:1].[Cl: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[O:18][C:19]([F:22])([F:21])[F:20])[C:8]([CH2:23][Cl:26])=[CH:7]2

Participants

4

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 57707874HCID 57707874, compound

Product 1

HCID 86630637HCID 86630637, compound

Procedure

A solution of (8-chloro-2-(2-(trifluoromethoxy)phenyl)quinolin-3-yl)methanol (0.5470 g, 1.546 mmol) in chloroform (5.155 mL, 1.546 mmol) was treated with thionyl chloride (0.5626 mL, 7.732 mmol) dropwise, and the reaction mixture was stirred at room temperature. After 2.5 h, the mixture was concentrated under reduced pressure and co-evaporated three times with CH2Cl2 to give 8-chloro-3-(chloromethyl)-2-(2-(trifluoromethoxy)phenyl)quinoline hydrochloride as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.75 (1 H, s), 8.10 (1 H, dd, J=8.2, 1.2 Hz), 8.03 (1 H, dd, J=7.5, 1.3 Hz), 7.64-7.74 (3 H, m), 7.53-7.63 (2 H, m), 4.75 (2 H, br. s.), 89676-3-1-1H-NMR; LC-MS (ESI) m/z 372.0 [M+H]+ (Exact Mass of neutral form: 371.009). The yellow syrup was carried on crude without purification for the next step.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cc50b0ad8edc4446840db42f9cea3026
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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