Water → HCID 11522235, compound

HRID 1172833Notes

Reaction equation

HRID 1172833 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[N:11]=[C:10]([O:20][C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Product 1

HCID 11522235HCID 11522235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from Step 1 (54 g, 0.26 mol), p-chlorophenol (31.7 g, 0.25 mol) and cesium carbonate (101.4 g, 0.31 mol) in anhydrous DMF (1.0 L) was stirred at 25° C. for about 2 h or until less than 5% of the starting material remained. The reaction mixture was then poured into water (2.5 L) and extracted with ethyl acetate (2×800 mL). The organic layer was washed with water (2×300 mL) and dried over magnesium sulfate. The crude product was purified by chromatography on silica gel eluting with 7:1 hexane:ethyl acetate to afford the title product.

Workup

  1. extractionextracted with ethyl acetate (2×800 mL)
  2. washThe organic layer was washed with water (2×300 mL)
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product was purified by chromatography on silica gel eluting with 7:1 hexane

Sources & evidence

ORD record
ord-5cd4cded891e47379c63424a46ec1498
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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