Sulfuric Acid → HCID 178497281, compound

HRID 1072846Notes

Reaction equation

HRID 1072846 reaction equation
S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH3:11][O:12][C:13]([C:15]1[CH:23]=[C:22]2[C:18]([C:19](C)([CH2:24]O)[NH:20][NH:21]2)=[CH:17][CH:16]=1)=[O:14]>>[CH3:11][O:12][C:13]([C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH3:24])=[N:20][NH:21]2)=[CH:17][CH:16]=1)=[O:14]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86585543HCID 86585543, compound

Product 1

HCID 178497281HCID 178497281, compoundYield 87%

Procedure

6-(Methoxycarbonyl)-3-methyl-1H-indazole methanol (50 ml), and concentrated sulfuric acid (0.1 ml) was added. The mixture was heated under reflux for 22 hr. After cooling, a saturated aqueous sodium hydrogencarbonate solution was added and the methanol was distilled away under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure to give the objective compound (340 mg, 87%) as brown crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 22 hr
  3. temperatureAfter cooling
  4. distillationthe methanol was distilled away under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe drying agent was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e9b9269c4c764c6a931ccb5a7fd9e321
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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