Ethanol → HCID 66523890, compound

HRID 1880413Notes

Reaction equation

HRID 1880413 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.OS(O)(=O)=O.[CH3:19][CH2:20]O>CCOC(C)=O>[OH:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:19][CH3:20])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 669202967-Hydroxy-1H-indazole-5-carboxylic acid

Product 1

HCID 66523890HCID 66523890, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-hydroxy-1H-indazole-5-carboxylic acid (1.08 g, 6.06 mmol) in EtOH (50 mL) containing conc. H2SO4 (0.34 mL) was heated at reflux overnight. The mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3. The aqueous phase was back extracted with EtOAc (3×). The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to afford ethyl 7-hydroxy-1H-indazole-5-carboxylate (918 mg, 73%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washwashed with saturated aqueous NaHCO3
  4. extractionThe aqueous phase was back extracted with EtOAc (3×)
  5. washThe combined organic extracts were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3a1c6bb8134f41b4a5ad72ddff466126
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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