m-Chloroperbenzoic acid → 2-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)quinoline 1-oxide

HRID 892591노트

반응식

HRID 892591 반응식
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1([CH3:35])[CH:18]=[C:17]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)[C:16]2[CH:29]=[C:30]([C:33]#[N:34])[CH:31]=[CH:32][C:15]=2[O:14]1>ClCCl>[C:33]([C:30]1[CH:31]=[CH:32][C:15]2[O:14][C:13]([CH3:35])([CH3:12])[CH:18]=[C:17]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N+:20]=3[O-:9])[C:16]=2[CH:29]=1)#[N:34]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 198956232,2-dimethyl-4-(2-quinolyl)-2H-1-benzopyran-6-carbonitrile

생성물 1

HCID 198956762-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)quinoline 1-oxide수율 6.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

450 mg of m-chloroperbenzoic acid were added at room temperature to a solution of 624 mg of 2,2-dimethyl-4-(2-quinolyl)-2H-1-benzopyran-6-carbonitrile in 20 ml of dichloromethane. After stirring at room temperature for 6 hours the mixture was washed with sodium bicarbonate solution and the organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (4:1) for the elution and then chromatographed on silica gel a second time using methanol/ethyl acetate (1:9) for the elution. The product was recrystallized from toluene to give 45 mg of 2-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)quinoline 1-oxide of melting point 177° C.

후처리

  1. washwas washed with sodium bicarbonate solution
  2. dry with materialthe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution
  6. customchromatographed on silica gel a second time
  7. washfor the elution
  8. customThe product was recrystallized from toluene

출처 및 근거

ORD 기록
ord-0251338e72a44a1b8fb614f171343aa6
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05118694

반응 노트

불러오는 중…