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Phenethyl bromide → 6-(2-Chlorophenyl)-3-methyl-1-(2-phenylethyl)-4,5,6,7-tetrahydroindazol-4-one

HRID 1700688
Notes
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Reaction equation

HRID 1700688 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:18][C:17]2[NH:16][N:15]=[C:14]([CH3:19])[C:13]=2[C:12](=[O:20])[CH2:11]1.[C:21]1([CH2:27][CH2:28]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:18][C:17]2[N:16]([CH2:28][CH2:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:15]=[C:14]([CH3:19])[C:13]=2[C:12](=[O:20])[CH2:11]1.[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:18][C:17]2[C:13](=[C:14]([CH3:19])[N:15]([CH2:28][CH2:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:16]=2)[C:12](=[O:20])[CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 1784341903-Methyl-6-(2-chlorophenyl)-4,5,6,7-tetrahydroindazol-4-one

Product 2

HCID 183175946-(2-Chlorophenyl)-3-methyl-1-(2-phenylethyl)-4,5,6,7-tetrahydroindazol-4-oneHCID 183176296-(2-Chlorophenyl)-3-methyl-2-(2-phenylethyl)-4,5,6,7-tetrahydroindazol-4-one

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.041 g, washed with hexane thrice) in dimethylformamide (10 ml) was added a solution of 6-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (0.4 g) in dimethylformamide (2 ml), and the mixture was stirred at room temperature for 40 minutes. To the mixture was added 2-phenylethyl bromide (0.30 g), and the mixture was stirred at the same temperature for 18 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (ethyl acetate-hexane) to give 6-(2-chlorophenyl)-3-methyl-1-(2-phenylethyl)-4,5,6,7-tetrahydroindazol-4-one (0.22 g) as colorless crystals and 6-(2-chlorophenyl)-3-methyl-2-(2-phenylethyl)-4,5,6,7-tetrahydroindazol-4-one (0.2 g) as oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 18 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-2994bd470998484a8e61ff94c65e8080
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06350749B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes