Diethyl 6-ethoxy-3-pyridylaminomethylenemalonate → Ethyl 6-ethoxy-1,4-dihydro-4-oxo-1,5-naphthyridine-3-carboxylate

HRID 2184754Notes

Reaction equation

HRID 2184754 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]=[C:12]([C:18]([O:20]CC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][N:5]=1)[CH3:2]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]1[N:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]2=[O:20])[CH3:2]

Participants

3

Reactant 1

HCID 621746Diethyl 6-ethoxy-3-pyridylaminomethylenemalonate

Product 1

HCID 604651Ethyl 6-ethoxy-1,4-dihydro-4-oxo-1,5-naphthyridine-3-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Diethyl (2-ethoxy-5-pyridylaminomethylene)malonate (6.04 g) was added to diphenyl ether (20 mL) preheated to 230° C. Heating was continued for 0.5 h, the reaction flask removed from the oil bath, and the mixture allowed to cool to ambient temperature. The product was triturated with 1:1 ether:hexanes, collected, rinsed with ether, and dried to give 2.98 g of ethyl 6-ethoxy-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate as a tan solid.

Workup

  1. custompreheated to 230° C
  2. temperatureHeating
  3. customthe reaction flask removed from the oil bath
  4. customThe product was triturated with 1:1 ether
  5. customhexanes, collected
  6. washrinsed with ether
  7. customdried

Sources & evidence

ORD record
ord-bbf7a10bd08840efbfd51a89b35aaa72
Source dataset
uspto-grants-2002_06
Patent number
US06399604B1

Reaction notes

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