Hydrogen Peroxide → HCID 86690771, compound

HRID 1471730Notes

Reaction equation

HRID 1471730 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[N:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=[O:26].[K+].[K+].OO.O>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:16]=[N:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]=1[C:11]([NH2:12])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 86690770HCID 86690770, compound

Product 1

HCID 86690771HCID 86690771, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 3,5-bis(benzyloxy)isonicotinonitrile (2.5 g, 7.9 mmol, 1 eq.) and K2CO3 (4.37 g, 31.6 mmol, 4 eq.) in DMSO (10 mL) was added H2O2 (30% in water, 2.0 mL) at rt. The mixture was stirred at rt O/N and added water (50 mL). The solid was collected and dried to give 3,5-bis(benzyloxy)isonicotinamide (2.2 g, 83%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.13 (s, 2H), 7.59-7.33 (m, 10H), 5.83 (s, 2H), 5.25 (s, 4H), 4.81 (s, 2H). LRMS (M+H+) m/z 335.1

Workup

  1. customThe solid was collected
  2. customdried

Sources & evidence

ORD record
ord-0f2809947e5c474b927ea683c6fbdd91
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

Loading…