반응식
CCCCCC.[Na].[C:8]([CH2:10][C:11]1[C:12]([C:17]#[N:18])=[N:13][CH:14]=[CH:15][CH:16]=1)#[N:9].[CH3:19][OH:20]>>[CH3:19][O:20][C:8]1[CH:10]=[C:11]2[C:12](=[C:17]([NH2:18])[N:9]=1)[N:13]=[CH:14][CH:15]=[CH:16]2참가 물질
반응 조건
- 온도
- 80 °C
실험 절차
To an oven-dried 250 mL flask under a nitrogen atmosphere was added anhydrous MeOH (200 mL). Na metal (1.07 g, 44 mmol) was weighed to a small beaker containing hexane and then transferred to the reaction vessel. After dissolution of the sodium, 3-cyanomethyl-pyridine-2-carbonitrile (5.3 g, 37 mmol) dissolved in anhydrous MeOH (10 mL) was added to the reaction. The resulting solution was heated at 80° C. for 3 hours, then stirred at room temperature overnight. The reaction mixture was concentrated to remove MeOH and extracted into CH2Cl2 (2×200 mL). The organic phases were combined, dried over Na2SO4, filtered, concentrated and unsuccessfully chromatographed (2% MeOH/CH2Cl2). The mixed fractions were combined and recrystalized from EtOAc/hexane affording 1.16 g (18%) of the title compound as a yellow solid. The mother liquor was rechromatographed (50% EtOAc/hexanes) to afford an additional 560 mg (9%) of product: mp decomposes above 110° C.; MS(+)APCI m/z 176 [M+H]+.
후처리
- additionwas added to the reaction
- concentrationThe reaction mixture was concentrated
- customto remove MeOH
- extractionextracted into CH2Cl2 (2×200 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customunsuccessfully chromatographed (2% MeOH/CH2Cl2)
- customrecrystalized from EtOAc/hexane affording 1.16 g (18%) of the title compound as a yellow solid
- customThe mother liquor was rechromatographed (50% EtOAc/hexanes)
출처 및 근거
- ORD 기록
- ord-ed1d3569d0d64f6b85ad9f56ed7c2aea
- 출처 데이터셋
- uspto-grants-2001_11
- 특허 번호
- US06313126B1
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