Malononitrile → HCID 178509182, compound

HRID 2304419Notes

Reaction equation

HRID 2304419 reaction equation
[F:1][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.FC1C=C(C=CC=1)N.C(#N)CC#N.O.[NH2:29][NH2:30]>>[NH2:14][C:13]1[C:10](=[N:9][NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[C:11]([NH2:12])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 97423-FluoroanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 4199695HCID 4199695, compound

Product 1

HCID 178509182HCID 178509182, compoundYield 37%

Procedure

This compound was prepared using 94 mg (0.5 mmol) of 2-[(3-fluorophenyl)-hydrazono]malononitrile, which was derived from 3-fluoroaniline (96 μL, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 5 min after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 41 mg (37%) of the title compound as a yellow solid. 1H NMR (ppm, DMSO-d6): 6.2 (br s, 4H), 7.0 (t, 1H), 7.35-7.62 (m, 3H), 10.80 (s, 1H).

Workup

  1. customThis compound was prepared
  2. customPrecipitate formed in the reaction tube approximately 5 min
  3. customThe resulting solid was isolated by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-c185693f4bcc4e60a2f6452c6ced7f1f
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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