Chloroform → HCID 68942948, compound

HRID 1397779Notes

Reaction equation

HRID 1397779 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[C:13]([CH3:18])=[N:14][CH:15]=[CH:16][CH:17]=1)[C:8]([CH:19](O)[CH3:20])=[CH:7]2.C(Cl)(Cl)[Cl:23].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[C:13]([CH3:18])=[N:14][CH:15]=[CH:16][CH:17]=1)[C:8]([CH:19]([Cl:23])[CH3:20])=[CH:7]2

Participants

4

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 57707769HCID 57707769, compound

Product 1

HCID 68942948HCID 68942948, compound

Procedure

A solution of 1-(8-chloro-2-(2-methylpyridin-3-yl)quinolin-3-yl)ethanol (1.1090 g, 3.712 mmol) in chloroform (12.37 mL, 3.712 mmol) was treated with thionyl chloride (1.350 mL, 18.56 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 8-chloro-3-(1-chloroethyl)-2-(2-methylpyridin-3-yl)quinoline hydrochloride as an off-white syrupy solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 (1 H, s), 8.94 (1 H, dd, J=5.7, 1.4 Hz), 8.56 (1 H, d, J=7.4 Hz), 8.19 (1 H, dd, J=8.2, 1.2 Hz), 8.07 (1 H, dd, J=7.4, 1.2 Hz), 8.02 (1 H, dd, J=7.6, 5.7 Hz), 7.71-7.77 (1 H, m), 5.25 (1 H, d, J=6.3 Hz), 2.52 (3 H, s), 1.92 (3 H, d, J=6.7 Hz); LC-MS (ESI) m/z 317.0 [M+H]+ (Exact Mass of neutral form: 316.053). The crude product was carried on crude without purification for the next step.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2a1ad36b822e41e7a80d0707494af4b4
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

Loading…