Dimethylformamide → 3-(2-Chloropyridin-4-yloxy)isonicotinonitrile

HRID 1972153Notes

Reaction equation

HRID 1972153 reaction equation
[H-].[Na+].CN(C=O)C.[OH:8][C:9]1[CH:16]=[N:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12].[Cl:17][C:18]1[CH:23]=[C:22]([N+]([O-])=O)[CH:21]=[CH:20][N:19]=1>O>[Cl:17][C:18]1[CH:23]=[C:22]([O:8][C:9]2[CH:16]=[N:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridineHCID 129590773-Hydroxypyridine-4-carbonitrile

Product 1

HCID 249946573-(2-Chloropyridin-4-yloxy)isonicotinonitrileYield 0.82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with sodium hydride (3.99 g, 158 mmol) and DMF (50 mL), and 3-hydroxyisonicotinonitrile (15.8 g, 132 mmol) was added. The reaction was stirred for 2 hours at ambient temperature. 2-Chloro-4-nitropyridine (21.9 g, 138 mmol) was added and the reaction was and stirred overnight. Water was added and the reaction was extracted with ethyl acetate. The organic layer was dried and concentrated. The crude product was purified by silica gel chromatography, eluting with DCM, 5% ammoniated methanol in DCM to give the desired product (0.250 g, 0.820% yield) as yellow solid.

Workup

  1. additionwas added
  2. stirringstirred overnight
  3. extractionthe reaction was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with DCM, 5% ammoniated methanol in DCM

Sources & evidence

ORD record
ord-a7a07dcbd2a44e0c8ce0d43b5db408fa
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

Loading…