Malononitrile → ethyl 3-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]benzoate

HRID 2095136Notes

Reaction equation

HRID 2095136 reaction equation
C(OC(=O)C1C=CC=C(N[N:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15])C=1)C.[NH2:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([O-:25])=[O:24].C(#N)[CH2:30][C:31]#N.O.[NH2:35][NH2:36]>>[CH2:30]([O:24][C:23](=[O:25])[C:22]1[CH:26]=[CH:27][CH:28]=[C:20]([NH:19][N:12]=[C:13]2[C:14]([NH2:15])=[N:36][N:35]=[C:16]2[NH2:17])[CH:21]=1)[CH3:31]

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 30141453-AminobenzoateHCID 857928413-(N'-dicyanomethylenehydrazino)benzoic acid ethyl ester

Product 1

HCID 178468921ethyl 3-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]benzoate

Procedure

3-[N′-(3,5-diaminopyrazol-4-ylidene)hydrazino]benzoic acid ethyl ester was prepared using 121 mg (0.5 mmol) of 3-(N′-dicyanomethylenehydrazino)benzoic acid ethyl ester, which was derived from 3-aminobenzoate (149 μL, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Precipitate formed in the reaction tube approximately 10 minutes after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 58 mg (42%) of the compound as a light brown solid.

Workup

  1. customPrecipitate formed in the reaction tube approximately 10 minutes
  2. customThe resulting solid was isolated by filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-b5e4d4ac65f34bfb916789ea3d92f205
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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