Sodium ethoxide → 6-Ethoxy-1,7-naphthyridin-8-amine

HRID 1881761노트

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HRID 1881761 반응식
[C:1]([CH2:3][C:4]1[C:5]([C:10]#[N:11])=[N:6][CH:7]=[CH:8][CH:9]=1)#[N:2].[O-:12][CH2:13][CH3:14].[Na+]>C(O)C>[CH2:13]([O:12][C:1]1[CH:3]=[C:4]2[C:5](=[C:10]([NH2:11])[N:2]=1)[N:6]=[CH:7][CH:8]=[CH:9]2)[CH3:14]

참가 물질

4

반응물 2

HCID 2723922Sodium ethoxideHCID 46725983-(Cyanomethyl)pyridine-2-carbonitrile

생성물 1

HCID 130013416-Ethoxy-1,7-naphthyridin-8-amine수율 14%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a 1 L round bottom flask was added 3-(cyanomethyl)picolinonitrile (3.56 g, 24.9 mmol), absolute ethanol (400 mL), followed by sodium ethoxide (11.1 mL, 21% solution w/v, 29.9 mmol). The mixture was stirred at reflux for 3 h. The solvent was then concentrated and the resultant residue was dissolved in ethyl acetate (200 mL), washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel to yield 6-ethoxy-1,7-naphthyridin-8-amine as a pale yellow solid (0.66 g, 3.49 mmol, 14%). 1H NMR (400 MHz, CDCl3): δ ppm 8.53 (dd, J=3.95, 1.76 Hz, 1H), 7.83 (dd, J=8.35, 1.76 Hz, 1H), 7.39 (dd, J=8.35, 4.39 Hz, 1H), 6.15 (s, 1H), 5.87 (br. s., 2H), 4.22 (q, J=7.03 Hz, 2H), 1.45 (t, J=7.03 Hz, 3H). LC/MS m/z 190 [M+H].

후처리

  1. temperatureat reflux for 3 h
  2. concentrationThe solvent was then concentrated
  3. dissolutionthe resultant residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel

출처 및 근거

ORD 기록
ord-4ecf20ef6a21421da66006594979d4be
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318941B2

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