Dichloromethane → 1-Methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride

HRID 641917

反応式

HRID 641917 の反応式
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[SH:12]([O:15]Cl)(=O)=[O:13].[Cl:17]CCl>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([Cl:17])(=[O:15])=[O:13])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 681091,2,3,4-Tetrahydro-1-methylquinolineHCID 178527254HCID 178527254、化合物

生成物 1

HCID 534141971-Methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride収率 8%

実験手順

A solution of 1-methyl-1,2,3,4-tetrahydroquinoline (10 g, 68.03 mmol) in dichloromethane (20 mL) was added dropwise to HSO3Cl (80 g, 689.66 mmol) at 0-5° C., and the resulting solution was maintained at room temperature overnight. The reaction mixture was then quenched by adding 300 mL of iced water. The resulting solution was extracted using ethyl acetate (3×150 mL). The organic layers were combined, concentrated, and the residue was purified by column chromatography using a 1:20 ethyl acetate/petroleum ether solvent system to afford 1-methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride as a yellow liquid in 8% yield. 1H NMR (CDCl3) δ 7.19 (d, 1H), 7.10 (d, 1H), 7.06 (s, 1H), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H).

後処理

  1. customThe reaction mixture was then quenched
  2. additionby adding 300 mL of iced water
  3. extractionThe resulting solution was extracted
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-0b5a9f789336410781473493566b8633
出典データセット
uspto-grants-2010_04
特許番号
US07696229B2

関連ノート

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