Aniline → 4-(3,5-Diamino-4-Phenylazopyrazol-1-Yl)Benzoic Acid

HRID 254979Notes

Reaction equation

HRID 254979 reaction equation
[C:1]1([NH:7][N:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C=CC=CC=1.C(#N)CC#N.[NH:26]([C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1)[NH2:27]>>[NH2:11][C:10]1[C:9]([N:8]=[N:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([NH2:13])[N:26]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:35][CH:36]=2)[N:27]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 8010MalononitrileHCID 120894-Hydrazinobenzoic acidHCID 67541Carbonyl cyanide phenylhydrazone

Product 1

HCID 1357440804-(3,5-Diamino-4-Phenylazopyrazol-1-Yl)Benzoic Acid

Procedure

4-(3,5-diamino-4-phenylazopyrazol-1-yl)benzoic acid was prepared using 85 mg (0.5 mmol) of 2-(phenylhydrazono)malononitrile, which was derived from aniline (10 mL, 107 mmol) and malononitrile (161 mmol), and 4-hydrazinobenzoic acid (76 mg, 0.5° mmol). After reacting for 4 hrs, the reaction remained as a slurry; however, analysis of the reaction solution by TLC indicated that no starting material remained. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 22 mg (14%) of the compound as a brown solid.

Workup

  1. customThe resulting solid was isolated by filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-c09e64d20c664c0e98bd7c197dfc4733
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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