2-[(6-Methyl-pyridin-3-ylamino)-methylene]-malonic acid diethyl ester → HCID 178469545, compound

HRID 968735Notes

Reaction equation

HRID 968735 reaction equation
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[N:12][C:13]2[C:14]([C:4]=1[OH:20])=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[O:7])[CH3:10]

Participants

3

Reactant 1

HCID 686164372-[(6-Methyl-pyridin-3-ylamino)-methylene]-malonic acid diethyl ester

Product 1

HCID 178469545HCID 178469545, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

The suspension of 2-[(6-methyl-pyridin-3-ylamino)-methylene]-malonic acid diethyl ester (24.0 g, 86.23 mmol) in diphenylether (300 mL) was heated under refluxing for 3 hrs. After cooling to room temperature, the reaction mixture was poured into nHexane (1000 mL) and the solid was collected by filtration to give 4-hydroxy-6-methyl-[1,5]naphthyridine-3-carboxylic acid ethyl ester (8.3 g, 42%). HR-MS-EI (+) m/e calcd for C12H12N2O3 (M+) 232.0848. found 232.0846.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 3 hrs
  3. additionthe reaction mixture was poured into nHexane (1000 mL)
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-670a7af75b794d7f8ccf9ad7c88a29d5
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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