Ammonia → HCID 68679112, compound

HRID 2233229Notes

Reaction equation

HRID 2233229 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=1[O:19][CH3:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)[Cl:22].N>C(OCC)(=O)C>[ClH:22].[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[O:19][CH3:20])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24479Stannous ChlorideHCID 269057N-(2-methoxy-4-nitrophenyl)benzamide

Product 1

HCID 68679112HCID 68679112, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzoyl 2-methoxy-4-nitroaniline (2.63 g, 9.66 mmol) and tin (II) chloride (10.9 g, 48.3 .mmol) were heated in ethyl acetate (200 ml) at reflux for 4 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. The orange solid was dissolved in ethyl acetate (45 ml) and a 1.0 N solution of hydrogen chloride in diethyl ether (25 ml) was added, causing precipitation of a white solid. Recrystallisation of this solid from methanol/ethyl acetate, yielded N-benzoyl 2-methoxy-4-aminoaniline hydrochloride (1.06 g, 39% yield) as a white crystalline solid:

Workup

  1. temperatureat reflux for 4 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. dissolutionThe orange solid was dissolved in ethyl acetate (45 ml)
  6. additiona 1.0 N solution of hydrogen chloride in diethyl ether (25 ml) was added
  7. customprecipitation of a white solid
  8. customRecrystallisation of this solid from methanol/ethyl acetate

Sources & evidence

ORD record
ord-289d2ab88c8243a2ae67128e95c434e3
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

Loading…