1,3-Dibromopropane → HCID 178422511, compound

HRID 647520Notes

Reaction equation

HRID 647520 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.[OH-].[Na+].[Br:19][CH2:20][CH2:21][CH2:22]Br>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[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

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 6104125-Methyl-3-phenyl-1H-indazole

Product 1

HCID 178422511HCID 178422511, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

5-Methyl-3-phenylindazole (400 g) was dissolved in toluene (1 l) and 1,3-dibromopropane (600 ml), and to the solution were added triethylbenzylammonium chloride (40 g) and 30% aqueous sodium hydroxide (800 ml). The mixture was heated at 60° C. for 30 minutes while stirring and the resulting organic layer was separated. The layer was washed with water, dried over sodium sulfate and then heated at reflux for 3 hours. The precipitate was recovered by filtration and washed with toluene to give 319 g of 2,3-dihydro-7-methyl-9-phenyl-1H-pyrazolo[1,2-a]indazolium bromide. The product which was recrystallized from water had a decomposition point of 239° C.

Workup

  1. customthe resulting organic layer was separated
  2. washThe layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. temperatureheated
  5. temperatureat reflux for 3 hours
  6. filtrationThe precipitate was recovered by filtration
  7. washwashed with toluene

Sources & evidence

ORD record
ord-014ad74bba364189b23895467a559b4f
Source dataset
uspto-grants-1983_10
Patent number
US04409234

Reaction notes

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