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

HRID 892591ノート

反応式

HRID 892591 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0251338e72a44a1b8fb614f171343aa6
出典データセット
uspto-grants-1992_06
特許番号
US05118694

反応ノート

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