Ammonia → N-(4-amino-2-methylphenyl)benzamide

HRID 2233227Notes

Reaction equation

HRID 2233227 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=1[CH3:19])(=[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[CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24479Stannous ChlorideHCID 2835288N-(2-methyl-4-nitrophenyl)benzamide

Product 1

HCID 3245571N-(4-amino-2-methylphenyl)benzamideYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzoyl 2-methyl-4-nitroaniline (2.93 g, 11.4 mmol) and tin (II) chloride (12.9 g, 57.2 mmol) were heated in ethyl acetate (100 ml) at reflux for 2 hours under an inert atmosphere. The reaction was allowed to cool to ambient temperature and concentrated aqueous ammonia (20 ml) was added. The reaction was filtered, the solid material was washed with ethyl acetate (3×30 ml) and then the combined organic layers were evaporated in vacuo. Drying of the resultant solid in vacuo, yielded N-benzoyl 2-methyl-4-aminoaniline (1.03 g, 40% yield) as a white 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-90a21e47eec34958ad2883162a8952b0
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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