Ethyl 4-[2-(4-pyridyl)hydrazino]-1,6-naphthyridine-3-carboxylate hydrochloride → HCID 178479607, compound

HRID 638243Notes

Reaction equation

HRID 638243 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[N:17][CH:18]=3)[N:13]=[CH:12][C:11]=2[C:20]([O:22]CC)=O)=[CH:4][CH:3]=1>C(O)CCC>[ClH:1].[N:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:22])[C:11]3=[CH:12][NH:13][C:14]4[CH:15]=[CH:16][N:17]=[CH:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 20253598Ethyl 4-[2-(4-pyridyl)hydrazino]-1,6-naphthyridine-3-carboxylate hydrochloride

Product 1

HCID 178479607HCID 178479607, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of ethyl 4-[2-(4-pyridyl)hydrazino]-1,6-naphthyridin-3-carboxylate hydrochloride (1.76 g) in 50 ml of n-butanol is refluxed for 20 hours. The mixture is cooled down to room temperature and filtered. Collected solid is dissolved in aqueous sodium hydroxide and stirred at room temperature for 21 hours, then filtered. The filtrate is acidified with 1N hydrochloric acid to precipitate a solid, which is collected, washed successively with aqueous methanol, methanol and acetone to yield 2-(4-pyridyl)-pyrazolo[4,3-c][1,6]naphthyridin-3(5H)-one hydrochloride, m.p. above 345°; IR (KBr) 726, 746, 791, 833, 898 cm-1.

Workup

  1. temperatureis refluxed for 20 hours
  2. filtrationfiltered
  3. customCollected solid
  4. dissolutionis dissolved in aqueous sodium hydroxide
  5. filtrationfiltered
  6. customto precipitate a solid, which
  7. customis collected
  8. washwashed successively with aqueous methanol, methanol and acetone

Sources & evidence

ORD record
ord-6a3f93875a7c4770a6bafa46461946c3
Source dataset
uspto-grants-1985_12
Patent number
US04560689

Reaction notes

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