3-Nitroaniline → HCID 178509186, compound

HRID 2095150Notes

Reaction equation

HRID 2095150 reaction equation
[N+](C1C=C(N[N:11]=[C:12]([C:15]#[N:16])[C:13]#[N:14])C=CC=1)([O-])=O.[N+:17]([C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23])([O-:19])=[O:18].C(#N)CC#N.O.[NH2:33][NH2:34]>>[N+:17]([C:20]1[CH:21]=[C:22]([NH:23][N:11]=[C:12]2[C:13]([NH2:14])=[N:34][N:33]=[C:15]2[NH2:16])[CH:24]=[CH:25][CH:26]=1)([O-:19])=[O:18]

Participants

5

Reactant 4

HCID 74233-NitroanilineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)HCID 910608(3-Nitrophenyl)carbonohydrazonoyl dicyanide

Product 1

HCID 178509186HCID 178509186, compound

Procedure

4-[(3-Nitrophenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 2-[(3-nitrophenyl)hydrazono]malononitrile (0.107 g, 0.5 mmol) which was derived from 3-nitroaniline (0.133 g, 1.0 mmol) and malononitrile (1.5 mmol) in a manner similar to that described in Example 2, and hydrazine hydrate. The resulting solid (0.088 g) was isolated by filtration, a portion (0.060 g) of which was purified by flash chromatography to yield 0.024 g (28%) of the title compound as an orange solid; MS (m/z, ES+): 248.0 (M+1, 100%).

Sources & evidence

ORD record
ord-f5cd81245da24161a32e33eb9903d20e
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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