2-Cyano-3-(6-methyl-pyridin-3-ylamino)-acrylic acid ethyl ester → 6-Methyl-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carbonitrile

HRID 968712Notes

Reaction equation

HRID 968712 reaction equation
C(O[C:4](=[O:17])[C:5]([C:15]#[N:16])=[CH:6][NH:7][C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[CH:12][CH:13]=1)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:14][C:11]1[N:10]=[C:9]2[C:8](=[CH:13][CH:12]=1)[NH:7][CH:6]=[C:5]([C:15]#[N:16])[C:4]2=[O:17]

Participants

3

Reactant 1

HCID 7219982-Cyano-3-(6-methyl-pyridin-3-ylamino)-acrylic acid ethyl ester

Product 1

HCID 587242946-Methyl-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carbonitrileYield 54.8%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

The suspension of 2-cyano-3-(6-methyl-pyridin-3-ylamino)-acrylic acid ethyl ester (8.8 g, 38.05 mmol) in diphenylether (190 mL) was heated under refluxing for 5 hrs. After cooling to room temperature, the reaction mixture was poured into nHexane (800 mL) and the solid was collected by filtration and washed with cold THF to give 6-methyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carbonitrile (3.86 g, 54.8%). HR-MS-EI (+) m/e calcd for C10H7N3O (M+) 185.0589. found 185.0591.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 5 hrs
  3. additionthe reaction mixture was poured into nHexane (800 mL)
  4. filtrationthe solid was collected by filtration
  5. washwashed with cold THF

Sources & evidence

ORD record
ord-716e3669cdb843ed8f7819372e347114
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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