Ethanol → HCID 178469297, compound

HRID 1880356Notes

Reaction equation

HRID 1880356 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:17]([O-:19])=[O:18])=[CH:10][C:11]=2[O:13]C(=O)C)[C:6]([CH2:20][CH3:21])=[N:5]1)(=O)C.[H-].[Na+].[CH2:24](O)[CH3:25]>CCOC(C)=O>[CH2:20]([C:6]1[C:7]2[C:12](=[C:11]([OH:13])[CH:10]=[C:9]([C:17]([O:19][CH2:24][CH3:25])=[O:18])[CH:8]=2)[NH:4][N:5]=1)[CH3:21]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 24758Sodium hydrideHCID 86650489HCID 86650489, compound

Product 1

HCID 178469297HCID 178469297, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-acetyl-7-(acetyloxy)-3-ethyl-1H-indazole-5-carboxylate (4.0 g, 13 mmol) in ethanol (450 mL) was slowly added 60% NaH (0.50 g, 12.6 mmol). The mixture was stirred for 1 hour before concentration and removal of the majority of the ethanol. The residue was taken up in EtOAc and washed with saturated aqueous NaHCO3. The aqueous phase was back extracted with EtOAc (2×). The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated. The solid was triturated with CH2Cl2 to provide ethyl 3-ethyl-7-hydroxy-1H-indazole-5-carboxylate as an off-white solid (2.9 g, 87%).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. extractionThe aqueous phase was back extracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solid was triturated with CH2Cl2

Sources & evidence

ORD record
ord-492c051e52df4d4181c3e52f2ebe411e
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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