Ammonia → HCID 43548871, compound

HRID 2233230Notes

Reaction equation

HRID 2233230 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=1[C:19]#[N:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)Cl.N>C(OCC)(=O)C>[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[C:19]#[N:20])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24479Stannous ChlorideHCID 11780487HCID 11780487, compound

Product 1

HCID 43548871HCID 43548871, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzoyl 2-cyano-4-nitroaniline (3.38 g, 12.6 mmol) and tin (II) chloride (14.3 g, 63.2 mmol) were heated in ethyl acetate (200 ml) at reflux for 2.5 hours under an inert atmosphere. The reaction was allowed to cool to ambient temperature, concentrated aqueous ammonia (20 ml) added and the reaction was then filtered. Evaporation of the organic layer in vacuo yielded N-benzoyl 2-cyano-4-aminoaniline (2.64 g, 88% yield) as a yellow solid:

Workup

  1. temperatureat reflux for 2.5 hours under an inert atmosphere
  2. filtrationthe reaction was then filtered
  3. customEvaporation of the organic layer in vacuo

Sources & evidence

ORD record
ord-2c659eb834b24fb5990f3d1cf26d5440
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

Loading…