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

HRID 2074519ノート

反応式

HRID 2074519 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  1. concentrationthe mixture was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-61e5bdeca98e4d278270cd3c86d110b2
出典データセット
uspto-grants-2011_04
特許番号
US07919498B2

反応ノート

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