3-Amino-5-(methanesulfonyl)benzoic acid → 3-Hydroxy-5-methylsulfonylbenzoic acid

HRID 1373104Notes

Reaction equation

HRID 1373104 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=[O:16].[Na+]>OS(O)(=O)=O.O>[OH:16][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 189525063-Amino-5-(methanesulfonyl)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 210741973-Hydroxy-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

3-Amino-5-methylsulphonylbenzoic acid (D12) (7.24 g) was dissolved in a mixture of conc H2SO4 (100 ml) and water (300 ml) and cooled to 5° C. sodium nitrite (5.1 g) in water (15 ml) was added dropwise and the mixture was thereafter stirred in the cooling bath for 15 min and with the cooling bath removed for 40 min. It was then heated at 90° C. for 1 h. The heating was removed and the reaction was allowed to stand overnight. The mixture was partially neutralised (˜pH1) with solid sodium bicarbonate until a solid precipitate formed. The mixture was extracted 3 times with ethyl acetate and the combined extracts were washed with water and brine, dried (Mg SO4) and evaporated to a solid which was triturated with ether to give D13 (2 crops, 4.12 g).

Workup

  1. additionwas added dropwise
  2. customremoved for 40 min
  3. customThe heating was removed
  4. waitto stand overnight
  5. customformed
  6. extractionThe mixture was extracted 3 times with ethyl acetate
  7. washthe combined extracts were washed with water and brine
  8. dry with materialdried (Mg SO4)
  9. customevaporated to a solid which
  10. customwas triturated with ether
  11. customto give D13 (2 crops, 4.12 g)

Sources & evidence

ORD record
ord-1d29e0d8cbc24ac58e46059b6ac9f679
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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