HCID 19374339, compound → HCID 19374295, compound

HRID 128631Notes

Reaction equation

HRID 128631 reaction equation
Cl.C([O:4][C:5]1[N:14]=[C:13]2[C:8]([C:9]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)C>[OH-].[Na+]>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:9]2[C:8]3[CH:7]=[CH:6][C:5](=[O:4])[NH:14][C:13]=3[N:12]=[CH:11][C:10]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 19374339HCID 19374339, compound

Product 1

HCID 19374295HCID 19374295, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 7-ethoxy-4-(4-methoxyanilino)-1,8-naphthyridine-3-carboxylate hydrochloride (2.6 g) and 5M sodium hydroxide solution (60 ml) was heated on a steam bath for 4 hours. The mixture was cooled and filtered. The residue was dissolved in IMS and hydrogen chloride gas bubbled through this solution. Ether was added to induce crystallisation and the mixture was filtered to give ethyl 4-[4-methoxyanilino]-7-oxo-7,8-dihydro-1,8-naphthyridine-3-carboxylate 0.3 hydrochloride hemihydrate, m.p. 243°-246° C.

Workup

  1. temperaturewas heated on a steam bath for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. dissolutionThe residue was dissolved in IMS
  5. customhydrogen chloride gas bubbled through this solution
  6. additionEther was added
  7. customcrystallisation
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-accee4d048a54ba7a4465482d978d2c0
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Reaction notes

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