2,6-Dimethylphenol → HCID 57942130, compound

HRID 1898128Notes

Reaction equation

HRID 1898128 reaction equation
Br[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[OH:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:11][C:5]1[CH:6]=[C:7]([NH2:8])[C:2]([O:20][C:14]2[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:13]=2[CH3:12])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 113352,6-DimethylphenolHCID 11430Potassium CarbonateHCID 2806812-Bromo-5-chloro-3-nitropyridine

Product 1

HCID 57942130HCID 57942130, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Bromo-3-nitro-5-chloropyridine (4.8 g, 20 mmol) and 2,6-dimethylphenol (5.0 g, 41 mmol) were magnetically stirred in dry DMF (65 mL) and potassium carbonate (11.0 g, 80 mmol) was added. The mixture was heated at 50° C. for 4 days, allowed to cool to room temperature and added to ice; the product was extracted with ethyl acetate (3×100 mL). The extracts were washed with saturated aqueous NaHCO3 and dried (MgSO4), filtered and concentrated to provide the desired product.

Workup

  1. temperatureto cool to room temperature
  2. additionadded to ice
  3. extractionthe product was extracted with ethyl acetate (3×100 mL)
  4. washThe extracts were washed with saturated aqueous NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4fe816742f8143fd85a5d9a1f98bf386
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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