1,3-Dibromopropane → HCID 178422511, compound

HRID 647519Notes

Reaction equation

HRID 647519 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+].[Br:19][CH2:20][CH2:21][CH2:22]Br>CN(C)C=O>[Br-:19].[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:6]3[CH2:22][CH2:21][CH2:20][N+:7]3=2)[CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 6104125-Methyl-3-phenyl-1H-indazole

Product 1

HCID 178422511HCID 178422511, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-methyl-3-phenylindazole (10.4 g) in dimethylformamide (60 ml), 50% sodium hydride (2.5 g) was added and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was then added dropwise to dimethylformamide (20 ml) containing 1,3-dibromopropane (25 g) while cooling with ice, and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was extracted with xylene (120 ml), and the extract was washed with water, dried over anhydrous sodium sulfate and heated at reflux for 2 hours. The resulting precipitate was recovered by filtration, and washed with acetone to give 9.2 g of 2,3-dihydro-7-methyl-9-phenyl-1H-pyrazolo[1,2-a]indazolium bromide. After recrystallization from isobutanol, the product had a melting point of 237° to 241° C. (decomposition).

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  3. extractionThe mixture was extracted with xylene (120 ml)
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. temperatureheated
  7. temperatureat reflux for 2 hours
  8. filtrationThe resulting precipitate was recovered by filtration
  9. washwashed with acetone

Sources & evidence

ORD record
ord-da71262dc11a4cd4ab32a7cf4700bd8b
Source dataset
uspto-grants-1983_10
Patent number
US04409234

Reaction notes

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