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

HRID 1986429노트

반응식

HRID 1986429 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 688333146-Hydroxy-4-phenyl-2-propylquinoline-3-carbonitrile수율 56%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ff61c76a1bb24130b897e26ad54355ac
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547710B2

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