Water → HCID 136335133, compound

HRID 1247011Notes

Reaction equation

HRID 1247011 reaction equation
[OH:1][C@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5]1.[N:15]([O-])=[O:16].[Na+].O>C(O)(=O)C>[OH:1][C@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[C:11]=2[N:15]=[O:16])[CH:6]=[N:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 136335134HCID 136335134, compound

Product 1

HCID 136335133HCID 136335133, compoundYield 465.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-[(R)-2-hydroxypropyl]-1H-indazol-6-ol (2.0 g, 1.04 mmol) in acetic acid (20 mL) was added sodium nitrite (0.72 g, 10.4 mol) and the mixture was stirred at room temperature for 1 hour. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2×200 mL). The combined extracts were washed with water (200 mL), and a saturated aqueous solution of sodium bicarbonate (200 mL), dried over magnesium sulfate, filtered and evaporated to a residue which was purified by chromatography (silica gel, hexane/ethyl acetate gradient) to give a red solid (1.07 g, 47%): LC/MS m/z 222.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×200 mL)
  2. washThe combined extracts were washed with water (200 mL)
  3. dry with materiala saturated aqueous solution of sodium bicarbonate (200 mL), dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to a residue which
  6. customwas purified by chromatography (silica gel, hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-be731a9284ef403c907c380ebada564b
Source dataset
uspto-grants-2006_10
Patent number
US07129257B1

Reaction notes

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