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

HRID 1881761ノート

反応式

HRID 1881761 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 130013416-Ethoxy-1,7-naphthyridin-8-amine収率 14%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-4ecf20ef6a21421da66006594979d4be
出典データセット
uspto-grants-2012_11
特許番号
US08318941B2

反応ノート

読み込み中…