2-Amino-3-nitrobenzoic acid → Methyl 2-amino-3-nitrobenzoate

HRID 2109998Notes

Reaction equation

HRID 2109998 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14](=O)(O)[O-].[Na+]>CO.S(=O)(=O)(O)O>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 2196332-Amino-3-nitrobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

After dissolving 2-amino-3-nitrobenzoic acid (1.00 g, 5.49 mmol) in methanol (40 ml), sulfuric acid (0.50 ml) was added and the mixture was heated to reflux for 2 days. The reaction mixture was cooled to room temperature, and then the pH was adjusted to approximately 9 with saturated aqueous sodium bicarbonate and the mixture was concentrated under reduced pressure to approximately 10 ml. Water (20 ml) was added, the mixture was extracted with ethyl acetate (10 ml×3 times), and the obtained organic layer was dried over anhydrous magnesium sulfate. It was then concentrated under reduced pressure, and the produced crystals were dried to obtain 2-amino-3-nitrobenzoic acid methyl ester. The compound was identified by NMR.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 days
  4. concentrationthe mixture was concentrated under reduced pressure to approximately 10 ml
  5. additionWater (20 ml) was added
  6. extractionthe mixture was extracted with ethyl acetate (10 ml×3 times)
  7. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
  8. concentrationIt was then concentrated under reduced pressure
  9. customthe produced crystals were dried

Sources & evidence

ORD record
ord-0e0a4a981e6f4cf28f4754694d93981e
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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