Hydrogen Peroxide → 4-(6,6-Dimethyl-4-oxo-3-methyl-4,5,6,7-tetrahydroindazol-1-yl)-2-(3,4,5-trimethoxyanilino)-benzamide

HRID 602398Notes

Reaction equation

HRID 602398 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:10][C:9]2[N:8]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([NH:19][C:20]4[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=4)[CH:12]=3)[N:7]=[C:6]([CH3:32])[C:5]=2[C:4](=[O:33])[CH2:3]1.C([OH:37])C.CS(C)=O.[OH-].[Na+].OO>O>[CH3:1][C:2]1([CH3:34])[CH2:10][C:9]2[N:8]([C:11]3[CH:18]=[CH:17][C:14]([C:15]([NH2:16])=[O:37])=[C:13]([NH:19][C:20]4[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=4)[CH:12]=3)[N:7]=[C:6]([CH3:32])[C:5]=2[C:4](=[O:33])[CH2:3]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22338741Dimethylsulfoxide ethanolHCID 669528904-(6,6-Dimethyl-4-oxo-3-methyl-4,5,6,7-tetrahydro-indazol-1-yl)-2-(3,4,5-trimethoxyanilino)benzonitrile

Product 1

HCID 118544344-(6,6-Dimethyl-4-oxo-3-methyl-4,5,6,7-tetrahydroindazol-1-yl)-2-(3,4,5-trimethoxyanilino)-benzamideYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-(6,6-dimethyl-4-oxo-3-methyl-4,5,6,7-tetrahydro-indazol-1-yl)-2-(3,4,5-trimethoxyanilino)-benzonitrile (1.56 g, 3.39 mmol, 1.0 eq.) in 17 mL of a mixture of 4:1 ethanol-dimethyl sulfoxide was added 2 mL of 1 M aqueous sodium hydroxide and 2 mL of 30% hydrogen peroxide. After 3 hours the reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound, 4-(6,6-dimethyl-4-oxo-3-methyl-4,5,6,7-tetrahydro-indazol-1-yl)-2-(3,4,5-trimethoxyanilino)-benzamide, (1.61 g, 99%) as a tan solid: LC/MS (m/z): [M+H]+ 479.3.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3be7b8e8aadb4800a1e8d4af81960f12
Source dataset
uspto-grants-2011_03
Patent number
US07906529B2

Reaction notes

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