Hydrazine hydrate (1:1) → 6-(4-benzylamino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

HRID 1619966Notes

Reaction equation

O.[NH2:2][NH2:3].[CH2:4]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH:19]([CH3:24])[CH2:20][C:21](O)=[O:22])=[CH:14][C:13]=1[OH:26])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)(=O)C>[CH2:4]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]([CH3:24])[CH2:20][C:21](=[O:22])[NH:2][N:3]=2)=[CH:14][C:13]=1[OH:26])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 110 °C

Procedure

While cooling with the ice bath 69.9 ml (1396 mmol) hydrazine hydrate are added dropwise to 220 ml glacial acetic acid, then 54.7 g (175 mmol) 4-(4-benzylamino-3-hydroxy-phenyl)-3-methyl-4-oxo-butyric acid are added and the mixture is stirred for 1.5 h at 110° C. Then the mixture is cooled somewhat and poured onto ice water, the precipitated product is suction filtered, washed first with copious amounts of water, then with a little acetone and then dried in the vacuum dryer.

Workup

temperatureThen the mixture is cooled somewhat
additionpoured onto ice water
filtrationfiltered
washwashed first with copious amounts of water
dry with materialwith a little acetone and then dried in the vacuum dryer

Sources & evidence

ORD record: ord-01efdea66a83440794839b1af17bcc3a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772323B2

Reaction notes

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