Acetic Acid → Methyl 3-amino-4-(methylamino)benzoate

HRID 1410209Notes

Reaction equation

HRID 1410209 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-])=O.CC(O)=O.C([O-])(O)=O.[Na+]>[Fe].CO>[NH2:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[NH:2][CH3:1])[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 7650848Methyl 4-(methylamino)-3-nitrobenzoate

Product 1

HCID 15586064Methyl 3-amino-4-(methylamino)benzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

Fe powder (3.4 g, 60 mmol) was added to a mixture of methyl 4-methylamino-3-nitrobenzoate (2.5 g, 12.0 mmol), AcOH (10 mL) and MeOH (100 mL) at reflux. The mixture was heated at reflux for 30 min and allowed to cool to rt. The pH was adjusted to ˜8 by addition of NaHCO3 (aq, sat) and the mixture was filtered through Celite. The filter cake was washed with EtOH and the combined filtrates were concentrated and the residue extracted with EtOAc. The combined extracts were washed with brine, dried and concentrated to give the sub-title compound. Yield: 1.91 g (88%)

Workup

  1. temperatureat reflux
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 30 min
  4. filtrationthe mixture was filtered through Celite
  5. washThe filter cake was washed with EtOH
  6. concentrationthe combined filtrates were concentrated
  7. extractionthe residue extracted with EtOAc
  8. washThe combined extracts were washed with brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-79f3a213d9e74f50bd834f6c320ff149
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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