Ammonium Chloride → 1-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile

HRID 17889

반응식

HRID 17889 반응식
Br[C:2]1[C:3](=[O:27])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][CH:7]=[C:6]([O:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:5]=2.[Cu][C:29]#[N:30].[Cl-].[NH4+]>CN(C)C=O>[O:27]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([O:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:5]=2)[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:2]1[C:29]#[N:30]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 686950762-Bromo-3-phenyl-6-(3-phenylpropoxy)indene-1-oneHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 686950891-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile수율 83.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

2-Bromo-3-phenyl-6-(3-phenylpropoxy)indene-1-one (1.0 g, 2.3 mmol) was dissolved in N,N-dimethylformamide (10 ml). Copper (I) cyanide (617 mg, 6.9 mmol) was added thereto and the mixture was stirred for 3 hours at 150° C. The mixture was cooled, and saturated ammonium chloride was added thereto. The organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:3) to obtain the title compound (700 mg, yield 80%) as a red solid.

후처리

  1. temperatureThe mixture was cooled
  2. extractionThe organic layer was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:3)

출처 및 근거

ORD 기록
ord-be4c3fb850964b1bb1e28c3c67e9cbba
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741323B2

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