2-Chloroaniline → HCID 178509176, compound

HRID 2304440Notes

Reaction equation

HRID 2304440 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12].ClC1C=CC=CC=1N.C(#N)CC#N.O.[NH2:29][NH2:30]>>[NH2:14][C:13]1[C:10](=[N:9][NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:11]([NH2:12])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 72402-ChloroanilineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 108744[(2-chlorophenyl)hydrazono]malononitrile

Product 1

HCID 178509176HCID 178509176, compoundYield 29%

Procedure

This compound was prepared using 102 mg (0.5 mmol) of 2-[(2-chlorophenyl)-hydrazono]malononitrile, which was derived from 2-chloroaniline (105 μL, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 10 min after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 34 mg (29%) of the title compound as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-aee7169b1880440e85c6e6f991738243
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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