Acetic Acid → n-(1-Ethoxy)cyclopropyl-3,4-difluoro-2-methoxyaniline

HRID 1275928Notes

Reaction equation

HRID 1275928 reaction equation
[F:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[C:12]([OH:15])(=O)[CH3:13].C(O[C:19]1(O[Si](C)(C)C)[CH2:21][CH2:20]1)C>C(O)C>[CH2:12]([O:15][N:5]([CH:19]1[CH2:21][CH2:20]1)[C:4]1[CH:6]=[CH:7][C:8]([F:9])=[C:2]([F:1])[C:3]=1[O:10][CH3:11])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 111374253,4-Difluoro-2-methoxyaniline

Product 1

HCID 88022372n-(1-Ethoxy)cyclopropyl-3,4-difluoro-2-methoxyanilineYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 200-ml four-necked flask provided with a reflux condenser, a thermometer and a stirrer were fed 7.96 g (0.05 mol) of 3,4-difluoro-2-methoxyaniline, 40 g (0.67 mol) of acetic acid and 100 ml of ethanol. To the resulting mixture being stirred at room temperature was dropwise added 9.24 g (0.053 mol) of 1-ethoxy-1-trimethylsilyloxycyclopropane. The resulting mixture was placed on an oil bath and refluxed at 80° C. for 3 hours with stirring, in a nitrogen current. The resulting reaction mixture was concentrated under aspirator vacuum by the use of a rotary evaporator. Lastly, the acetic acid remaining in the resulting residue was removed by the use of a vacuum pump to obtain 11.5 g of an oily substance. This oily substance was subjected to vacuum distillation to obtain 10.1 g (yield: 83.0%) of N-(1-ethoxy)cyclopropyl-3,4-difluoro-2-methoxyaniline.

Workup

  1. customInto a 200-ml four-necked flask provided with a reflux condenser
  2. customThe resulting mixture was placed on an oil bath
  3. temperaturerefluxed at 80° C. for 3 hours
  4. stirringwith stirring, in a nitrogen current
  5. customThe resulting reaction mixture
  6. concentrationwas concentrated under aspirator vacuum by the use of a rotary evaporator
  7. customLastly, the acetic acid remaining in the resulting residue was removed by the use of a vacuum pump
  8. customto obtain 11.5 g of an oily substance
  9. distillationThis oily substance was subjected to vacuum distillation

Sources & evidence

ORD record
ord-eb7be823d3ae4ae0916a96df4c1dcda2
Source dataset
uspto-grants-2000_12
Patent number
US06162944

Reaction notes

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