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

HRID 1881761Notes

Reaction equation

HRID 1881761 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-4ecf20ef6a21421da66006594979d4be
Source dataset
uspto-grants-2012_11
Patent number
US08318941B2

Reaction notes

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