Potassium Carbonate → HCID 67253527, compound

HRID 2042062Notes

Reaction equation

HRID 2042062 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:7]#[N:8])([O-])=O.[Cl:15][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[N:20][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([O:22][C:4]2[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=2)[C:7]#[N:8])[CH:19]=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20062Benzonitrile, 3,5-dinitro-HCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 67253527HCID 67253527, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-dinitro-benzonitrile (5 g, 25.9 mol), 5-chloro-pyridin-3-ol (3.35 g, 25.9 mol) and K2CO3 (7.2 g, 52 mol) in DMF (150 mL) was heated at 100° C. overnight. The mixture was concentrated in vacuo and the residue was poured into water. The aqueous layer was extracted with ethyl acetate (3×150 mL) and the combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography to afford 3-(5-chloro-pyridin-3-yloxy)-5-nitro-benzonitrile (3.1 g, 44% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.56 (s, 1H), 8.51 (s, 1H), 8.47 (s, 1H), 8.22 (s, 1H), 8.19 (s, 1H), 7.87 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was poured into water
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×150 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e8babb5ae8194fb490cfe6826e29da35
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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