Aniline → HCID 135709857, compound

HRID 2304444Notes

Reaction equation

HRID 2304444 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.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(#N)CC#[N:24].N(C1C=CC([C:32]([OH:34])=[O:33])=CC=1)N>>[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:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:32]([OH:34])=[O:33])[N:24]=1

Participants

5

Reactant 4

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

Product 1

HCID 135709857HCID 135709857, compoundYield 14%

Procedure

This compound 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) as described in Example 8, 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 title compound as a brown solid.

Workup

  1. customThis compound was prepared
  2. customThe resulting solid was isolated by filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-4ce7e25bd3ae48689f61b2a864e8ffca
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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