Ethanol → 1031417-54-5

HRID 1880422Notes

Reaction equation

HRID 1880422 reaction equation
[Cl:1][C:2]1[CH:3]=C(C#N)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[OH-:13].[K+].[CH2:15]([OH:17])[CH3:16]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:16]([C:15]([OH:13])=[O:17])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 669205317-Chloro-1H-indazole-5-carbonitrile

Product 1

HCID 582525981031417-54-5

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of 7-chloro-1H-indazole-5-carbonitrile (250 mg, 1.41 mmol) in ethanol/water (3:1 ration, 15 mL) was added potassium hydroxide (395 mg, 7.04 mmol) and the mixture was heated at reflux. After 3 houra, the majority of the ethanol was allowed to distill off, additional potassium hydroxide (614 mg) was added and heating was continued for overnight. The reaction mixture was cooled to room temperature, washed with Et2O (3×20 mL) and the organic extract was acidified with 1 N HCl. The resultant precipitate was isolated by vacuum filtration, washed with water (about 15 mL) and heptane (about 15 mL), dried at room temperature/0.5 mmHg to provide the title compound (221 mg, 79.7%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. distillationto distill off
  4. additionadditional potassium hydroxide (614 mg) was added
  5. temperatureheating
  6. washwashed with Et2O (3×20 mL)
  7. extractionthe organic extract

Sources & evidence

ORD record
ord-90815d8336d34f5c8d880964f170559e
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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