Potassium Carbonate → HCID 67236094, compound

HRID 1505342Notes

Reaction equation

HRID 1505342 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 109535825-Methoxy-2-methylphenol2×

Product 1

HCID 67236094HCID 67236094, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-methyl-5-(methyloxy)phenol (Intermediate 12, 2 g) and 2-chloro-5-nitropyridine (2.1 g, 13.2 mmol) in DMF (50 mL) was added potassium carbonate (2.76 g, 20 mmol) and the reaction mixture was stirred at 100° C. overnight. The mixture was evaporated under vacuum and water (100 mL) was added. It was extracted with ethyl acetate (3 times 100 mL) and the combined organic layers were dried over sodium sulphate and evaporated to afford a brown oil, which was purified by column chromatography on silica gel (mobile phase: EtOAc/PE=1/50−1/20) to give the title compound (1.5 g).

Workup

  1. customThe mixture was evaporated under vacuum and water (100 mL)
  2. additionwas added
  3. extractionIt was extracted with ethyl acetate (3 times 100 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulphate
  5. customevaporated
  6. customto afford a brown oil, which
  7. customwas purified by column chromatography on silica gel (mobile phase: EtOAc/PE=1/50−1/20)

Sources & evidence

ORD record
ord-3c8b44c1f7f14cc7a799df5dbf1cfe39
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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