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

HRID 1925611Notes

Reaction equation

HRID 1925611 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. The mixture was heated at 120° C. with stirring in an autoclave for 1 day, cooled to room temperature (RT), added to ice 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 in a 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-e1d839bdf293477d8f4cae4b771768b2
Source dataset
uspto-grants-2012_05
Patent number
US08178695B2

Reaction notes

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