Potassium Carbonate → Methyl 2-[4-(5-chloro-3-nitropyridin-2-yloxy)phenoxy]propionate

HRID 845700Notes

Reaction equation

HRID 845700 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1.[OH:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(#N)C>[Cl:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([O:12][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:24][CH:25]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl esterHCID 80633312,5-Dichloro-3-nitropyridine

Product 1

HCID 20129975Methyl 2-[4-(5-chloro-3-nitropyridin-2-yloxy)phenoxy]propionateYield 93.1%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

38.6 g (0.20 mole) of 2.5-dichloro-3-nitropyridine, 41.2 g (0.21 mole) of methyl 2-(4-hydroxyphenoxy)propionate, 400 ml of acetonitrile, 35.9 g (0.26 mole) of potassium carbonate and 0.33 g (0.002 mole) of potassium iodide are heated for 13 hours to 80° C. The reaction mixture is filtered and the filter cake is washed with acetonitrile. The filtrate is concentrated by evaporation and the residue is taken up in 500 ml of methylene chloride. After treating the solution with 15 g of activated carbon, it is filtered through a layer of silica gel and the filtrate is concentrated by evaporation. The residue is crystallised from a mixture of hexane and ethyl acetate, affording 65.7 g (93.1% of theory) of methyl 2-[4-(5-chloro-3-nitropyridin-2-yloxy)phenoxy]propionate with a melting point of 91°-92° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filter cake is washed with acetonitrile
  3. concentrationThe filtrate is concentrated by evaporation
  4. additionAfter treating the solution with 15 g of activated carbon, it
  5. filtrationis filtered through a layer of silica gel
  6. concentrationthe filtrate is concentrated by evaporation
  7. customThe residue is crystallised from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-c037bc55a449466694ace0f2654525a9
Source dataset
uspto-grants-1988_07
Patent number
US04759796

Reaction notes

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