Ethyl 5-oxohexanoate → Ethyl 4-(1,8-naphthyridin-2-yl)butanoate

HRID 1761036Notes

Reaction equation

HRID 1761036 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.O=[C:11]([CH3:20])[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].N1CCC[C@H]1C(O)=O>CCO>[N:1]1[C:2]2[C:3](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH:4]=[CH:20][C:11]=1[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 84130Ethyl 5-oxohexanoateHCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 10955797Ethyl 4-(1,8-naphthyridin-2-yl)butanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution consisting of 2-aminonicotinaldehyde (0.7 g; 5.8 mmol), ethyl 5-oxohexanoate (1.83 g; 11.6 mmol; 1.85 ml), L-proline (0.166 g; 1.45 mmol) and 50 ml of EtOH is heated at 90° C., with stirring, for 6 hours. The reaction mixture is then concentrated and the residue is purified by chromatography on silica gel (eluant: EtOAc) to yield the title product in the form of a beige solid.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. customthe residue is purified by chromatography on silica gel (eluant: EtOAc)

Sources & evidence

ORD record
ord-5119fa5279c84fc384c72bf7b2b4c6ae
Source dataset
uspto-grants-2005_01
Patent number
US06846833B2

Reaction notes

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