Hydrazine hydrate (1:1) → 6-(4-Amino-3-methylphenyl)-4,5-dihydropyridazin-3(2H)-one

HRID 65194Notes

Reaction equation

HRID 65194 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[CH3:15].O.[NH2:17][NH2:18]>Cl.C(O)C>[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[CH3:15].[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]2[CH2:8][CH2:9][C:10](=[O:11])[NH:17][N:18]=2)=[CH:4][C:3]=1[CH3:15]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 201629223-(4-Amino-3-methyl-benzoyl)-propionic acid

Product 2

HCID 148829156-(4-Amino-3-methylphenyl)-4,5-dihydropyridazin-3(2H)-oneHCID 201629223-(4-Amino-3-methyl-benzoyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

There are obtained from 70 g of N-acetyl-1,2-toluidine, with 47 g of succinic anhydride and 234 g of aluminium chloride in 2000 ml of tetrachloroethane, by the customary method, 50 g of 3-(3-methyl-4-acetamido-benzoyl)-propionic acid, m.p. 150°-160° C., as crude product. From this are obtained, by hydrolysis in 18% hydrochloric acid, 28 g of crude 3-(4-amino-3-methyl-benzoyl)-propionic acid. And from 6 g of 3-(4-amino-3-methyl-benzoyl)-propionic acid are obtained, with 1.7 ml of hydrazine hydrate in 70 ml of ethanol, in a manner analogous to that in Example 1, 2.6 g of 6-(4-amino-3-methyl-phenyl)-4,5-dihydro-3(2H)-pyridazinone having a melting point of 215°-225° C.

Sources & evidence

ORD record
ord-edc4c72db59940fda4c20636c0d9d133
Source dataset
uspto-grants-1986_09
Patent number
US04613599

Reaction notes

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