4-Nitro-o-anisic acid → 2-Methoxy-3,4-dinitrobenzoic Acid

HRID 1357041Notes

Reaction equation

HRID 1357041 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:13][CH3:14])[CH:5]=1)([O-:3])=[O:2].[N+:15]([O-])([OH:17])=[O:16].S(=O)(=O)(O)O>CS(C)=O>[CH3:14][O:13][C:6]1[C:5]([N+:15]([O-:17])=[O:16])=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 757764-Nitro-o-anisic acidHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 185048962-Methoxy-3,4-dinitrobenzoic Acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

4-Nitro-2-methoxybenzoic acid, 3.09 g, was added to 20 mL Nitric acid:Sulfuric acid 1:1, at 0° C. After addition was complete the reaction mixture was heated at 100 ° C. for 30 minutes. Cooled to room temperature and poured into 200 mL ice water. The aqueous layer was extracted with ethyl acetate and washed with saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated to give a yellow solid. This material was purified by chromatography on silica using ethyl acetate/hexane/methanol/acetic acid 5/5/1/0.1. The yellow solid obtained was used for the next step. EIMS M+ 242 (Exp. 242). NMR, d6 DMSO: s (1H) 8.5, s (1H) 7.95, s (3H) 4.05.

Workup

  1. additionAfter addition
  2. temperatureCooled to room temperature
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. customThis material was purified by chromatography on silica
  9. customThe yellow solid obtained

Sources & evidence

ORD record
ord-b3c7f89e196d40daaf69ad77fde15a80
Source dataset
uspto-grants-2003_07
Patent number
US06589954B1

Reaction notes

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