Acetic Acid → 6-(4-benzylamino-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

HRID 930552Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH:16]([CH3:21])[CH2:17][C:18](O)=[O:19])=[CH:11][C:10]=1[N+:23]([O-:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:27][NH2:28].C(O)(=O)C>C(O)C>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]([CH3:21])[CH2:17][C:18](=[O:19])[NH:27][N:28]=2)=[CH:11][C:10]=1[N+:23]([O-:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(4-Benzylamino-3-nitro-phenyl)-3-methyl-4-oxo-butyric acid E-4.1″ (939 mg; 2.74 mmol) is placed in 7 ml ethanol and treated with hydrazine hydrate (0.16 ml; 3.29 mmol) and acetic acid (78.58 μl; 1.37 mmol). The reaction mixture is heated up to 100° C. for 2 hours. Another portion of hydrazine hydrate (0.08 ml; 1.65 mmol) and 40 μl acetic acid are added and stirred for 2 hours at 100° C. After letting the reaction cooling to RT, the product precipitates. It is filtered off and washed with methanol and dried under reduced pressure.

Workup

temperaturecooling to RT
customthe product precipitates
filtrationIt is filtered off
washwashed with methanol
customdried under reduced pressure

Sources & evidence

ORD record: ord-43f285e70cfa4190b1449e64e1717aab
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296748B2

Reaction notes

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