Ammonia → HCID 679477, compound

HRID 2233225Notes

Reaction equation

HRID 2233225 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=1[Cl:19])(=[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[Cl:19])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24479Stannous ChlorideHCID 522117N-(2-Chloro-4-nitrophenyl)benzamide

Product 1

HCID 679477HCID 679477, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzoyl 2-chloro-4-nitroaniline (5.77 g, 20.8 mmol) and tin (II) chloride (23.5 g, 104 .mmol) were heated in ethyl acetate (250 ml) at reflux for 2 hours under an inert atmosphere. The reaction was allowed to cool to ambient temperature and concentrated aqueous ammonia (40 ml) was added. The reaction was filtered, the solid material was washed with ethyl acetate (3×30 ml) and the combined organic layers were evaporated in vacuo. Drying of the resultant solid in vacuo, yielded N-benzoyl 2-chloro-4-aminoaniline (4.63 g, 90% yield) as a cream-coloured crystalline solid:

Workup

  1. temperatureat reflux for 2 hours under an inert atmosphere
  2. filtrationThe reaction was filtered
  3. washthe solid material was washed with ethyl acetate (3×30 ml)
  4. customthe combined organic layers were evaporated in vacuo
  5. customDrying of the resultant solid in vacuo

Sources & evidence

ORD record
ord-aab54856548c429e847a7bd7302ef093
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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