Chlorosuccinimide → 3-Chloro-1H-indazole-5-carboxaldehyde

HRID 2384771Notes

Reaction equation

HRID 2384771 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[Cl:12]N1C(=O)CCC1=O>C(#N)C>[Cl:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=2)[NH:1][N:2]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 212506441H-Indazole-5-carboxaldehyde

Product 1

HCID 1785193763-Chloro-1H-indazole-5-carboxaldehydeYield 54.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
67.5 °C

Procedure

To a solution of 1H-Indazole-5-carbaldehyde (3.2 g, 21.89 mmol) in acetonitrile (140 mL) was added N-Chlorosuccinimide (3.5 g, 26.27 mmol). After stirring for 50 hours at 65 to 70° C., the precipitate was filtered, washed with cold acetonitrile, abundantly with water and dried to afford the title compound as a white solid (2.15 g, 54%).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with cold acetonitrile, abundantly with water
  3. customdried

Sources & evidence

ORD record
ord-dd9e039c818b4430982010d2043c931e
Source dataset
uspto-grants-2012_09
Patent number
US08263781B2

Reaction notes

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