Cesium carbonate → 2-Methyl-5-(2-methyl-4-nitrophenoxy)pyridine

HRID 877094

Reaction equation

HRID 877094 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[CH3:12][C:13]1[N:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[O:19][C:16]1[CH:15]=[CH:14][C:13]([CH3:12])=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 142752-Methyl-5-hydroxypyridineHCID 83315Benzene, 1-chloro-2-methyl-4-nitro-

Product 1

HCID 179901022-Methyl-5-(2-methyl-4-nitrophenoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 1-chloro-2-methyl-4-nitrobenzene (17.2 g), 6-methylpyridin-3-ol (12 g) and Cs2CO3 (39 g) in DMF (150 mL) was heated at 110° C. for 4 h. The solid was filtered and water (100 mL) and EtOAc (200 mL) were added. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained yellow solid was used for the next step directly.

Workup

  1. filtrationThe solid was filtered
  2. additionwater (100 mL) and EtOAc (200 mL) were added
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-33ca47bf8b6d4e3fa5d1d616b29da37c
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Linked notes

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