Water → 3-Methoxy-2-nitroaniline

HRID 1189113Notes

Reaction equation

HRID 1189113 reaction equation
C([N:3](CC)CC)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[CH3:27][O:28][C:29]1[C:30]([N+:38]([O-:40])=[O:39])=[C:31]([CH:35]=[CH:36][CH:37]=1)C(O)=O.O>C1(C)C=CC=CC=1>[CH3:27][O:28][C:29]1[C:30]([N+:38]([O-:40])=[O:39])=[C:31]([NH2:3])[CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 786323-Methoxy-2-nitrobenzoic acidHCID 123414Diphenylphosphoryl azide

Product 1

HCID 104647003-Methoxy-2-nitroanilineYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (6.29 mL) and diphenyl azidophosphate (6.66 mL, 30.1 mmol) were added to a suspension of 3-methoxy-2-nitrobenzoic acid (3.00 g, 15.2 mmol) in toluene (50 mL). The reaction mixture was stirred under reflux for 2 hours, water (10 mL) was added and it was stirred overnight under reflux. After evaporation of the solvent, the residue was dissolved in AcOEt and the resulting solution was filtered through celite. The organic phase was washed with saturated solution of NaHCO3, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 900 mg (5.35 mmol, 35%) of 3-methoxy-2-nitrophenylamine as a yellow solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. stirringit was stirred overnight
  3. temperatureunder reflux
  4. customAfter evaporation of the solvent
  5. dissolutionthe residue was dissolved in AcOEt
  6. filtrationthe resulting solution was filtered through celite
  7. washThe organic phase was washed with saturated solution of NaHCO3, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-128c2b58814c4e7192f57d7eea6c0156
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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