Malononitrile → HCID 178509187, compound

HRID 254946Notes

Reaction equation

HRID 254946 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]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 115683-AminophenolHCID 24654Hydrazine hydrate (1:1)HCID 12051877PROPANEDINITRILE, [(3-HYDROXYPHENYL)HYDRAZONO]-

Product 1

HCID 178509187HCID 178509187, compound

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), 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 compound as a black solid.

Workup

  1. temperatureAfter heating for 4 hrs
  2. customa small amount of solid had formed
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated to a gummy black solid
  5. dissolutionThis material was dissolved in ethyl acetate
  6. customa small amount of gummy solid was precipitated from the solution by the addition of hexanes
  7. customThe solid was removed by filtration
  8. concentrationthe filtrate was again concentrated
  9. customThe resulting solid was purified by flash chromatography
  10. washeluting with methylene chloride/methanol (7:1)

Sources & evidence

ORD record
ord-4071ffab64114886908c714ba0486f94
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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