Diphenyl Ether → Ethyl 7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 2378102Notes

Reaction equation

HRID 2378102 reaction equation
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC.C(OCC)(=O)C>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:20])[C:18]2[C:13](=[N:14][C:15]([CH3:19])=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 83264Diethyl [[(6-methyl-2-pyridyl)amino]methylene]malonate

Product 1

HCID 5373687Ethyl 7-methyl-4-oxo-1,8-naphthyridine-3-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Add 2-[(6-methyl-pyridin-2-ylamino)-methylene]-malonic acid diethyl ester (14.8 g) to the refluxing phenyl ether (100 ml) over a period of 5 min under nitrogen. After the addition is complete, keep the reaction under reflux for 3 h. Cool it to room temperature, and then pour the reaction mixture into 1:1 hexane/ethyl acetate (2000 ml). Collect the brown precipitate by filtration to obtain 7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (8.35 g, 72% for two steps). MS (ES+): 233 (M+H); (ES−): 231 (M−H).

Workup

  1. additionAfter the addition
  2. customthe reaction
  3. temperatureunder reflux for 3 h
  4. customCollect the brown precipitate
  5. filtrationby filtration

Sources & evidence

ORD record
ord-0c916daf51c047c795859eee3d31dea5
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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