Hydrazine, dihydrochloride → Ethyl 3-oxo-6-(pyridin-3-yl)-2,3-dihydropyridazine-4-carboxylate

HRID 970193Notes

Reaction equation

HRID 970193 reaction equation
C(O[C:9]1C=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:18](=[O:21])[NH:19][N:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl.Cl.[NH2:29]N>C(O)C>[N:29]1[CH:9]=[CH:10][CH:11]=[C:12]([C:15]2[CH:16]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:18](=[O:21])[NH:19][N:20]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 59018088Ethyl 6-[4-(benzyloxy)phenyl]-3-oxo-2,3-dihydropyridazine-4-carboxylate

Product 1

HCID 20527882Ethyl 3-oxo-6-(pyridin-3-yl)-2,3-dihydropyridazine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Working as in example 19 for the preparation of ethyl 6-[4-(benzyloxy)phenyl]-3-oxo-2,3-dihydropyridazine-4-carboxylate, but starting with 8.85 g of diethyl hydroxy(pyridin-3-oxoethyl)malonate, 3.67 g of hydrazine dihydrochloride and 250 cm3 of ethanol, and after recrystallization from ethanol, 3.6 g of ethyl 6-pyridin-3-yl-3-oxo-2,3-dihydropyridazine-4-carboxylate were obtained in the form of a green solid melting at a temperature in the region of 150° C.

Workup

  1. customafter recrystallization from ethanol

Sources & evidence

ORD record
ord-55f5d61476d24da9a729bf165b62d6ff
Source dataset
uspto-grants-2007_12
Patent number
US07309701B2

Reaction notes

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