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

HRID 1585573노트

반응식

HRID 1585573 반응식
[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

참가 물질

6

반응물 3

HCID 7412Benzoyl chlorideHCID 691636-ChloroquinolineHCID 82115Trimethylsilyl cyanide

생성물 1

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

시약·촉매·용매 2

HCID 6451240Aluminum(III) Chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b28014d7ac24484e83c9b1f972a3472e
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05939435

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