Sulfuric Acid → 3-Cyclopropylamino-2-methyl-4-(methylsulfonyl)benzoic acid

HRID 548524Notes

Reaction equation

HRID 548524 reaction equation
F[C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=[O:6].[CH:16]1([NH2:19])[CH2:18][CH2:17]1.S(=O)(=O)(O)O>>[CH:16]1([NH:19][C:2]2[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=2[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=[O:6])[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 69828CyclopropylamineHCID 142544793-Fluoro-2-methyl-4-(methylsulfonyl)benzoic acid

Product 1

HCID 574249453-Cyclopropylamino-2-methyl-4-(methylsulfonyl)benzoic acid

Conditions

Temperature
120 °C

Procedure

5.0 g (22 mmol) of 3-fluoro-2-methyl-4-(methylsulfonyl)benzoic acid were dissolved in 25.0 ml (356 mmol) of cyclopropylamine. With stirring, the mixture was then heated in an autoclave at 120° C. for 1 day, and then cooled to room temperature (RT), acidified with a mixture of ice-water and conc. sulfuric acid and extracted with ethyl acetate. The combined organic phases were dried over MgSO4, and the solvent was removed under reduced pressure. The residue was purified by preparative HPLC. This gave 1.8 g of a beige solid of purity of 95%.

Workup

  1. temperaturecooled to room temperature (RT)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-dbb00001c4bc416dac27fb72a49e131f
Source dataset
uspto-grants-2011_05
Patent number
US07943550B2

Reaction notes

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