1-Bromopropane → 1-Propyl-1H-indazole-3-carboxylic acid

HRID 1586452Notes

Reaction equation

HRID 1586452 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.[H-].[Na+].Br[CH2:16][CH2:17][CH3:18]>CN(C=O)C>[CH2:16]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 78250Indazole-3-carboxylic acid

Product 1

HCID 106320111-Propyl-1H-indazole-3-carboxylic acidYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indazole-3-carboxylic acid (5.00 g) in DMF (40 ml) was gradually added 60% sodium hydride (1.55 g) at 0° C. with stirring, and the mixture was stirred at room temperature for one hour. Then 1-bromopropane (4.55 g) was added, and the mixture was stirred overnight. The reaction solution was distilled off, dissolved in water, and washed with ethyl acetate. The aqueous layer was made acidic with hydrochloric acid, extracted with ethyl acetate, then the extract was dried over anhydrous magnesium sulfate, and decolorized with active carbon. After the solvent was distilled off, crystallization from ether gave the title compound (4.24 g) as crystals. Yield=67%.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for one hour
  3. stirringthe mixture was stirred overnight
  4. distillationThe reaction solution was distilled off
  5. dissolutiondissolved in water
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. dry with materialthe extract was dried over anhydrous magnesium sulfate
  9. distillationAfter the solvent was distilled off
  10. customcrystallization from ether

Sources & evidence

ORD record
ord-738ee3fc61c6471c95a8397993440009
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

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