Sulfuric Acid → 4-amino-2-methylbenzoic acid

HRID 1631914Notes

Reaction equation

HRID 1631914 reaction equation
C([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:14])[CH:6]=1)(=O)C.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>CO>[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:14])[CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 27352244-Acetamido-2-methylbenzoic acid

Product 1

HCID 2416324-amino-2-methylbenzoic acidYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-acetylamino-2-methyl-benzoic acid (25.5 g) in methanol (250 ml) was added conc. H2SO4 (19 ml) dropwise and the reaction heated to reflux. After 2.5 h, the reaction was cooled to rt. NaHCO3 (aq) was added until alkaline and the obtained mixture was extracted with EtOAc. The organic extracts were washed with NaOH(aq) (2 M) 3 times, then dried and concentrated affording 17.6 g of the title compound.

Workup

  1. temperaturethe reaction heated to reflux
  2. extractionthe obtained mixture was extracted with EtOAc
  3. washThe organic extracts were washed with NaOH(aq) (2 M) 3 times
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee11c71804b34a8ea8ae36729f664882
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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