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Water → 3-(5'-Nitro-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)propanenitrile

HRID 853887
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HRID 853887 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]12[O:18][CH2:17][CH2:16][CH2:15][O:14]1)([O-:3])=[O:2].[C:19](#[N:22])[CH:20]=[CH2:21].O>CN(C=O)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:21][CH2:20][C:19]#[N:22])[C:8](=[O:13])[C:7]12[O:18][CH2:17][CH2:16][CH2:15][O:14]1)([O-:3])=[O:2]
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참가 물질

6

반응물 3

HCID 962WaterHCID 7855AcrylonitrileHCID 337321165'-nitrospiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one

생성물 1

HCID 589325573-(5'-Nitro-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)propanenitrile수율 101.4%

시약·촉매·용매 2

HCID 66854Benzyltrimethylammonium hydroxide촉매
HCID 6228
Dimethylformamide
용매

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온도
52 °C

실험 절차

At room temperature, to a mixture of 5′-nitrospiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one(1.75 g, 6.99 mmol) and benzyltrimethylammonium hydroxide (40% aqueous solution, 0.110 mL, 0.699 mmol, 0.1 mole %) in DMF (31 mL) was added acrylonitrile (0.921 mL, 14.0 mmol, 2 eq) drop-wise. and the mixture was heated at 52° C. for 2 hr. The reaction was cooled to room temperature and poured into H2O (160 mL). The reaction mixture was extracted with Et2O. The combined organic extracts were washed with brine and concentrated. The crude product was purified on Biotage KP silica gel eluting with 96/4 CH2Cl2/CH3CN to give the title compound as a yellow solid (2.15 g, 100% ). NMR (300 Mz, DMSO-d6): consistent

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe reaction mixture was extracted with Et2O
  3. washThe combined organic extracts were washed with brine
  4. concentrationconcentrated
  5. customThe crude product was purified on Biotage KP silica gel eluting with 96/4 CH2Cl2/CH3CN

출처 및 근거

ORD 기록
ord-13df433d10e34e2a9f912a95b69e9fa0
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07256198B2

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