Hydrogen Peroxide → HCID 57748585, compound

HRID 906186Notes

Reaction equation

HRID 906186 reaction equation
[C:1]([C:3]1[C:11]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[C:5]([CH3:18])[N:4]=1)#[N:2].OO.C(=O)([O-])[O-:22].[K+].[K+].[OH-].[K+]>CS(C)=O.O.CO>[NH2:2][C:1]([C:3]1[C:11]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:18])[N:4]=1)=[O:22]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 86631952HCID 86631952, compound

Product 1

HCID 57748585HCID 57748585, compoundYield 348.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-cyano-2-methyl-5-(pentan-3-ylamino)nicotinate (0.543 g, 1.97 mmol) in DMSO (10 ml) were added 50% aqueous hydrogen peroxide (0.2441 g, 3.55 mmol) and potassium carbonate (0.068 g, 0.49 mmol) at 10° C. The reaction mixture was stirred at room temperature for two hours then a solution of potassium hydroxide (0.22 g, 3.94 mmol) in water (2 ml) and methanol (10 ml) were added to above reaction mixture. After being stirred for another two hours at 45° C., the reaction mixture was cooled to room temperature and neutralized to PH 7. 6-(Aminocarbonyl)-2-methyl-5-(pentan-3-ylamino)nicotinic acid (0.453 g, 87%) was obtained by filtration and drying. 1HNMR (400 MHz, MeOH-D4): 7.62 (s, 1H), 3.35 (m, 1H), 2.60 (s, 3H), 1.65 (m, 2H), 1.52 (m, 2H), 0.95 (t, J=7.20 Hz, 6H). MS (EI) for C13H20N3O3: 267.2 (MH+).

Workup

  1. stirringAfter being stirred for another two hours at 45° C.
  2. temperaturethe reaction mixture was cooled to room temperature and neutralized to PH 7

Sources & evidence

ORD record
ord-2516f0e326bd4ca9b75607537671dbe7
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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