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

HRID 1633248Notes

Reaction equation

HRID 1633248 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-c4dc5c95230343108da19f5bf761144a
Source dataset
uspto-grants-1984_10
Patent number
US04479955

Reaction notes

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