Hexanenitrile, 5-oxo- → HCID 21927832, compound

HRID 585546Notes

Reaction equation

HRID 585546 reaction equation
O=[C:2]([CH3:8])[CH2:3][CH2:4][CH2:5][C:6]#[N:7].[NH2:9][C:10]1[C:15]([CH:16]=O)=[CH:14][CH:13]=[CH:12][N:11]=1>C(O)C>[CH3:8][C:2]1[C:3]([CH2:4][CH2:5][C:6]#[N:7])=[CH:16][C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 82611Hexanenitrile, 5-oxo-HCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 21927832HCID 21927832, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-oxo-hexanenitrile (5 mL, TCI-US), 2-amino-3-formylpyridine (7 g, J. Org. Chem. 1983, vol.48, p3401) and ethanol (100 mL) was heated to reflux for 12 hours. Following evaporation of the solvent, the residue was chromatographed (silica gel, ethyl acetate) to give 4-[1,8]naphthyridin-2-yl-butyronitirile and the title product as colorless solids. 1H (CDCl3) δ 2.29 (3H, s); 2.83 (2H, t); 3.18 (2H, t); 7.48 (1H, dd); 8.04 (1H, s); 8.20 (1H, dd); 9.03 (1H, dd). Step 2

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. customevaporation of the solvent
  4. customthe residue was chromatographed (silica gel, ethyl acetate)
  5. customto give 4-[1,8]naphthyridin-2-yl-butyronitirile

Sources & evidence

ORD record
ord-760887f24401417490bba0073d70e238
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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