Benzoyl chloride → 1-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

HRID 1585573ノート

反応式

HRID 1585573 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[Si]([C:25]#[N:26])(C)C>C(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>[C:12]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]1[C:25]#[N:26])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 7412Benzoyl chlorideHCID 691636-ChloroquinolineHCID 82115Trimethylsilyl cyanide

生成物 1

HCID 133367791-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

試薬・触媒・溶媒 2

HCID 6451240Aluminum(III) Chloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 6-chloroquinoline (9.5 g), benzoyl chloride (13.2 g) in methylene chloride (50 mL) was treated with AlCl3 (0.10 g) followed by dropwise addition of trimethyl silyl cyanide (12.5 mL). After 0.5 hour, the mixture was diluted with 150 mL of methylene chloride and washed with water, 1N HCl, saturated sodium bicarbonate (aq.), and brine. The organic phase was dried over magnesium sulfate then evaporated to dryness. The residue was purified by column chromatography on silica gel using ethyl acetate/hexane (3:7) as the eluting solvent. The title compound (13 g) was obtained as a white solid, m.p. 141-143° C. This product was used for the preparation of the title compound described in step 2.

後処理

  1. washwashed with water, 1N HCl, saturated sodium bicarbonate (aq.), and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthen evaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-b28014d7ac24484e83c9b1f972a3472e
出典データセット
uspto-grants-1999_08
特許番号
US05939435

反応ノート

読み込み中…