Hexanenitrile, 5-oxo- → HCID 21927832, compound

HRID 1243509Notes

Reaction equation

HRID 1243509 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, p 3401) 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).

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-4a8b5ca972a447eb91d1c46705c91997
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

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