Water → 4-Chloro-1H-indazol-5-ol

HRID 1269840

Reaction equation

HRID 1269840 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[Cl:11]N1C(=O)CCC1=O.O>O1CCCC1>[Cl:11][C:5]1[C:6]([OH:10])=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[N:2][NH:1]2

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 1014381H-Indazol-5-ol

Product 1

HCID 229337834-Chloro-1H-indazol-5-olYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the 1H-indazol-5-ol (1.60 g, 0.0119 mol) obtained in Reference Example 4 in tetrahydrofuran (50 ml) was added N-chlorosuccinimide (1.59 g, 0.0119 mol) at room temperature. After 1 hour, the mixture thus obtained was heated to 40° C., and after another 2 hour, the mixture was heated to 50° C. After 5 hours, the reaction solution was poured into water (100 ml) and extracted with ethyl acetate (100 ml×3). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-chloro-1H-indazol-5-ol (1.7365 g, 86%).

Workup

  1. customthe mixture thus obtained
  2. waitafter another 2 hour
  3. temperaturethe mixture was heated to 50° C
  4. waitAfter 5 hours
  5. extractionextracted with ethyl acetate (100 ml×3)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5455ba8b632e4e768aec8f0d797e6a22
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Linked notes

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