2-Amino-5-nitrobenzonitrile → N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamide

HRID 583087Notes

Reaction equation

HRID 583087 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([C:9]#[N:10])[C:7]([NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>>[C:9]([C:8]1[CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[N:12]=[CH:15][N:16]([CH3:18])[CH3:17])#[N:10]

Participants

3

Reactant 2

HCID 285322-Amino-5-nitrobenzonitrileHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 10900084N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamide

Procedure

A 40.8 g portion of 5-nitro-anthranilonitrile and 40 ml of N,N-dimethylformamide dimethyl acetal were heated on a steam bath for 2 hours. The solvents were removed at reduced pressure and the residue was taken up in methylene chloride. After passing this solution through Magnesol the solvent was removed. After washing with ether 50.8 g of N'-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine was obtained.

Workup

  1. customThe solvents were removed at reduced pressure
  2. customwas removed
  3. washAfter washing with ether 50.8 g of N'-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine
  4. customwas obtained

Sources & evidence

ORD record
ord-b8fa8506e6ed46eba344059adfa4c35a
Source dataset
uspto-grants-1999_07
Patent number
US05929080

Reaction notes

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