HCID 18000191, compound → HCID 18000183, compound

HRID 479851Notes

Reaction equation

HRID 479851 reaction equation
C(O[C:4](=[O:27])[C:5](=[CH:11][NH:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:17][CH:18]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:20]([NH:19][C:16]1[N:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:4]2=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 18000191HCID 18000191, compound

Product 1

HCID 18000183HCID 18000183, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Diethyl(2-benzylamino-5-pyridylaminomethylene)malonate (2.23 g) was added to diphenyl ether (10 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 1.47 g of ethyl 6-benzylamino-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate as a brown 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-8ca7c74384d1481e853cfb3c3b0be241
Source dataset
uspto-grants-2003_11
Patent number
US06646124B2

Reaction notes

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