Dimethyl Sulfoxide → 6-(3,3-Dimethyl-1-oxo-indan-5-yloxy)-nicotinamide

HRID 747954Notes

Reaction equation

HRID 747954 reaction equation
OO.[CH3:3][C:4]1([CH3:23])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=3)[CH:11]=2)[C:6](=[O:22])[CH2:5]1.C([O-])([O-])=[O:25].[K+].[K+].CS(C)=O>O>[CH3:3][C:4]1([CH3:23])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]([NH2:19])=[O:25])=[CH:16][N:15]=3)[CH:11]=2)[C:6](=[O:22])[CH2:5]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 666728106-(3,3-Dimethyl-1-oxo-indan-5-yloxy)nicotinonitrile

Product 1

HCID 597506546-(3,3-Dimethyl-1-oxo-indan-5-yloxy)-nicotinamideYield 188.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 30% aqueous H2O2 (3.15 ml) to a suspension of 6-(3,3-Dimethyl-1-oxo-indan-5-yloxy)-nicotinonitrile (877 mg, 3.15 mmol), K2CO3 (218 mg, 1.57 mmol) and DMSO (10 ml) stirring under nitrogen at ambient temperature. After four hours, dilute the reaction mixture with water (100 ml) and extract with EtOAc (2×). Wash the extract with water and brine, dry (MgSO4) and concentrate on rotary evaporator to yield 876 mg of the title compound as an off-white solid. Mass spectrum (ion spray): m/z=297 (M+1); 1HNMR (CDCl3): 8.62 (s, 1H), 8.24 (d, 1H), 7.75 (d, 1H), 7.24 (s, 1H), 7.14 (d, 1H), 7.07 (d, 1H), 5.91 (broad, 2H), 2.63 (s, 2H), 1.43 (s, 6H).

Workup

  1. extractionextract with EtOAc (2×)
  2. washWash the
  3. extractionextract with water and brine
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate on rotary evaporator

Sources & evidence

ORD record
ord-15890b364cc54035a4f27a551a83663e
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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