Water → 6-Hydroxy-4-phenyl-2-propylquinoline-3-carbonitrile

HRID 1986429ノート

反応式

HRID 1986429 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si](C(C)(C)C)(C)C)=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.O=[C:25]([CH2:29][CH2:30][CH3:31])[CH2:26][C:27]#[N:28].CS(O)(=O)=O.O>C1(C)C=CC=CC=1>[OH:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:25]([CH2:29][CH2:30][CH3:31])[C:26]([C:27]#[N:28])=[C:16]2[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 97937233-OxohexanenitrileHCID 68832602(2-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanone

生成物 1

HCID 688333146-Hydroxy-4-phenyl-2-propylquinoline-3-carbonitrile収率 56%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanone (2.0 g, 6.1 mmol), 3-oxohexanenitrile (0.81 g, 7.3 mmol) and methanesulfonic acid (0.59 g, 6.1 mmol) in toluene (50 ml) was stirred at 110° C. for 15 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from disopropyl ether to give 6-hydroxy-4-phenyl-2-propylquinoline-3-carbonitrile (0.98 g, yield 56%) as pale-yellow crystals.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was crystallized from disopropyl ether

出典と根拠

ORDレコード
ord-ff61c76a1bb24130b897e26ad54355ac
出典データセット
uspto-grants-2009_06
特許番号
US07547710B2

反応ノート

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