Potassium Carbonate → 3-(3-Dimethoxymethyl-4-nitro-phenoxy)phenylamine

HRID 390265Notes

Reaction equation

HRID 390265 reaction equation
C([O-])([O-])=O.[K+].[K+].[NH2:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH:25]([O:28][CH3:29])[O:26][CH3:27])[CH:17]=1>C(O)C>[CH3:29][O:28][CH:25]([O:26][CH3:27])[C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[N+:22]([O-:24])=[O:23])[O:14][C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzene

Product 1

HCID 586250523-(3-Dimethoxymethyl-4-nitro-phenoxy)phenylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

K2CO3 (0.076 mol) was added to a mixture of 3-amino-phenol (0.069 mol) in ethanol (200 mL) and the mixture was stirred for 10 min at room temperature, then 4-chloro-2-dimethoxymethyl-1-nitro-benzene (0.046 mol) was added and the reaction mixture was stirred for 16 hours at reflux temperature. The mixture was allowed to reach room temperature and the solvent was evaporated. The residue was washed with water and extracted 2 times with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered off and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 100%). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred for 16 hours
  2. temperatureat reflux temperature
  3. customto reach room temperature
  4. customthe solvent was evaporated
  5. washThe residue was washed with water
  6. extractionextracted 2 times with CH2Cl2
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered off
  10. customthe solvent was evaporated
  11. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 100%)
  12. customThe purest product fractions were collected
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5e2e210c740a4168af8c9cc24d70bfe6
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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