Thionyl Chloride → 5-Chloro-3-(chloromethyl)-2-(2-(trifluoromethyl)phenyl)quinoline hydrochloride

HRID 2074519노트

반응식

HRID 2074519 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:22]O)[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])=[N:7]2.S(Cl)([Cl:26])=O>C(Cl)(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:22][Cl:26])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])=[N:7]2

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 67090613(5-Chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol

생성물 1

HCID 866266235-Chloro-3-(chloromethyl)-2-(2-(trifluoromethyl)phenyl)quinoline hydrochloride

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of (5-chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol (2.180 g, 6.455 mmol) in 22 mL of CHCl3 was treated with thionyl chloride (2.348 mL, 32.27 mmol) dropwise, and the reaction mixture was stirred at room temperature. After 1.5 hr, the mixture was concentrated under reduced pressure and co-evaporated three times with CH2Cl2 to give 5-chloro-3-(chloromethyl)-2-(2-(trifluoromethyl)phenyl)quinoline hydrochloride as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.86 (1 H, d, J=0.6 Hz), 7.99-8.05 (1 H, m), 7.94 (1 H, dd, J=7.4, 1.0 Hz), 7.88-7.92 (1 H, m), 7.81-7.87 (2 H, m), 7.74-7.81 (1H, m), 7.61-7.66 (1 H, m), 4.77 (2 H, d, J=79.0 Hz); LC-MS (ESI) m/z 356.0 and 358.0 [M+H]+ (Exact Mass of neutral form: 355.014). The yellow solid was carried on crude without purification for the next step.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-61e5bdeca98e4d278270cd3c86d110b2
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919498B2

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