Hydrogen Peroxide → 6-(1-Methylisoquinolin-4-yloxy)nicotinamide

HRID 2060857Notes

Reaction equation

HRID 2060857 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=2)=[CH:4][N:3]=1.C([O-])([O-])=[O:22].[K+].[K+].OO.O>CS(C)=O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]([NH2:18])=[O:22])=[CH:15][N:14]=2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 594012876-(1-Methylisoquinolin-4-yloxy)nicotinonitrile

Product 1

HCID 594013386-(1-Methylisoquinolin-4-yloxy)nicotinamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-(1-methylisoquinolin-4-yloxy)nicotinonitrile (Preparation 18) (200 mg, 0.77 mmol) in DMSO (5 mL) was added K2CO3 (53 mg, 0.38 mmol) and H2O2 (30% w/v, 120 μL, 1.1 mmol). After 1 h water (20 mL) was added and the mixture extracted with EtOAc (3×50 mL). The organic phase was washed with water (2×30 mL), NaHCO3 (30 mL), brine (30 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (0.5 NH3: 5 MeOH: 95 DCM) to give the title compound: RT=2.11 min; m/z (ES+)=280.1 [M+H]+.

Workup

  1. extractionthe mixture extracted with EtOAc (3×50 mL)
  2. washThe organic phase was washed with water (2×30 mL), NaHCO3 (30 mL), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customSolvent was removed in vacuo
  5. customthe residue purified by column chromatography (0.5 NH3: 5 MeOH: 95 DCM)

Sources & evidence

ORD record
ord-1c394ec21de2439fad5da58dc33d9de3
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

Loading…