Malononitrile → HCID 178509187, compound
Reaction equation
O[C:2]1[CH:3]=[C:4]([NH:8][N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.NC1C=C(O)C=CC=1.C(#N)CC#N.[OH2:28].[NH2:29][NH2:30]>>[NH2:12][C:11]1[C:10](=[N:9][NH:8][C:4]2[CH:5]=[C:6]([OH:28])[CH:7]=[CH:2][CH:3]=2)[C:13]([NH2:14])=[N:30][N:29]=1Participants
Procedure
3-[N′-(3,5-Diaminopyrazol-4-ylidene)hydrazino]phenol was prepared using 93 mg (0.5 mmol) of 2-[(3-hydroxyphenyl)hydrazono]malononitrile, which was derived from 3-aminophenol (109 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. After heating for 4 hrs, a small amount of solid had formed. The solid was filtered off and the filtrate was concentrated to a gummy black solid. This material was dissolved in ethyl acetate and a small amount of gummy solid was precipitated from the solution by the addition of hexanes. The solid was removed by filtration and the filtrate was again concentrated. The resulting solid was purified by flash chromatography eluting with methylene chloride/ methanol (7:1) to yield 45 mg (33%) of the title compound as a black solid.
Workup
- custom3-[N′-(3,5-Diaminopyrazol-4-ylidene)hydrazino]phenol was prepared
- temperatureAfter heating for 4 hrs
- customa small amount of solid had formed
- filtrationThe solid was filtered off
- concentrationthe filtrate was concentrated to a gummy black solid
- dissolutionThis material was dissolved in ethyl acetate
- customa small amount of gummy solid was precipitated from the solution by the addition of hexanes
- customThe solid was removed by filtration
- concentrationthe filtrate was again concentrated
- customThe resulting solid was purified by flash chromatography
- washeluting with methylene chloride/ methanol (7:1)
Sources & evidence
- ORD record
- ord-5cba73a79aed48e5b78a1b5bea4b1a60
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06436915B1
Reaction notes
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