Phenylhydrazine → HCID 178479605, compound

HRID 638240Notes

Reaction equation

HRID 638240 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=O.[C:17]1([NH:23][NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[ClH:1].[C:17]1([N:23]2[C:12](=[O:14])[C:3]3=[CH:4][NH:5][C:6]4[CH:7]=[CH:8][N:9]=[CH:10][C:11]=4[C:2]3=[N:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 17608818Ethyl 4-chloro-1,6-naphthyridine-3-carboxylate

Product 1

HCID 178479605HCID 178479605, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.60 g of ethyl 4-chloro-1,6-naphthyridine-3-carboxylate and 1.25 g of phenylhydrazine in 32 ml of methanol is stirred at 22° for 18 hours, then refluxed for 3 hours. The resultant slurry is allowed to cool down to room temperature and filtered, obtaining 2-phenyl-pyrazolo[4,3-c][1,6]-naphthyridin-3(5H)-one hydrochloride, mp 310°; IR (KBr) 750, 756, 777, 802, 843 cm-1. This hydrochloride salt is dissolved in 1N sodium hydroxide and filtered. Ammonium chloride (10 g) is added to the filtrate, the resulting precipitate is collected, and is crystallized from methanol to yield the free base, 2-phenyl-pyrazolo[4,3-c][1,6]naphthyridin-3(5H)-one, m.p. 334°-337°.

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-23039a5e59a74579a2e883f42802197c
Source dataset
uspto-grants-1985_12
Patent number
US04560689

Reaction notes

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