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

HRID 638244Notes

Reaction equation

HRID 638244 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][CH2:15][CH3:16])=[O:13].Cl.[NH:18]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[NH2:19]>CO>[ClH:1].[N:23]1[CH:24]=[CH:25][C:20]([NH:18][NH:19][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[N:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 17608818Ethyl 4-chloro-1,6-naphthyridine-3-carboxylateHCID 223202584-Hydrazinylpyridine hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.36 g of ethyl 4-chloro-1,6-naphthyridine-3-carboxylate and 1.53 g of 4-hydrazinopyridine hydrochloride in 37 ml of methanol is stirred for 19 hours at room temperature, then refluxed for 4 hours. The reaction mixture is then cooled in an ice bath, and solid is collected by filtration, washed successively with methanol and ether to yield ethyl 4-[2-(4-pyridyl)hydrazino]-1,6-naphthyridine-3-carboxylate hydrochloride.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureThe reaction mixture is then cooled in an ice bath
  3. filtrationsolid is collected by filtration
  4. washwashed successively with methanol and ether

Sources & evidence

ORD record
ord-ff3c296005414280960658dec3114101
Source dataset
uspto-grants-1985_12
Patent number
US04560689

Reaction notes

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