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

HRID 1068963Notes

Reaction equation

HRID 1068963 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-93d15966f7c2412f84184a8b5fa21724
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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