Potassium Carbonate → HCID 90019760, compound

HRID 2200098Notes

Reaction equation

HRID 2200098 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.Cl[C:10]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:16][C:15]1[C:10]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)=[N:11][CH:12]=[C:13]([N+:17]([O-:19])=[O:18])[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 896482-Chloro-3-methyl-5-nitropyridineHCID 178507942HCID 178507942, compound

Product 1

HCID 90019760HCID 90019760, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix 2-aminopyridin-4-ol (3.3 g, 30 mmol), 2-chloro-3-methyl-5-nitropyridine (5.17 g, 30 mmol) in anhydrous DMF (50 mL), add K2CO3 (8.28 g, 60 mmol). Stir the reaction at 90° C. overnight. Concentrate under reduced pressure to give crude product. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (3.3 g, 45%). MS: (M+1): 247.1.

Workup

  1. customthe reaction at 90° C. overnight
  2. concentrationConcentrate under reduced pressure
  3. customto give crude product
  4. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-2d4c080a63a3481b80d9c57e47d87828
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

Loading…