Sodium hydride → HCID 67485726, compound

HRID 1809593Notes

Reaction equation

HRID 1809593 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:13]=[C:14]([N+]([O-])=O)[C:15]([C:18]#[N:19])=[N:16][CH:17]=1.[NH4+].[Cl-]>O.CN(C=O)C>[Br:11][C:12]1[CH:13]=[C:14]([O:8][C:7]2[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[C:15]([C:18]#[N:19])=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 707192-Methylpyridin-3-olHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 67485726HCID 67485726, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A flask was charged with 2-methylpyridin-3-ol (3.0 g, 27.5 mmol) and DMF (100 mL). Sodium hydride (0.760 g, 30.2 mmol) was added and stirred for 5 minutes. 5-Bromo-3-nitropicolinonitrile (6.26 g, 27.5 mmol) was added and stirred for 10 minutes. The reaction was poured into a flask containing 300 mL saturated NH4Cl and 300 mL water with vigorous stirring. The solids were filtered and dried under high vacuum to afford 5-bromo-3-(2-methylpyridin-3-yloxy)picolinonitrile (7.78 g, 97.6% yield) as light tan solid.

Workup

  1. stirringstirred for 10 minutes
  2. additionThe reaction was poured into a flask
  3. filtrationThe solids were filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-ae987f96a4374487854f4f6ae5c64ebc
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

Loading…