Sodium Sulfate → HCID 53747454, compound

HRID 481307Notes

Reaction equation

HRID 481307 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:19]([O:21][C:22]([C:24]1[C:25]([Cl:30])=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23])[CH3:20]>ClCCl>[CH2:19]([O:21][C:22]([C:24]1[C:25]([Cl:30])=[N+:26]([O-:9])[CH:27]=[CH:28][CH:29]=1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acid2×HCID 2796614Ethyl chloronicotinate

Product 1

HCID 53747454HCID 53747454, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (mCPBA), prepared by suspending 41.4 g (0.021 mol) of 50% mCPBA in 100 ml of dichloromethane, adding a drying agent (sodium sulfate), and removing the solids by filtration, was added dropwise to a solution of 22.2 g (0.12 mol) of 2-chloro-3-pyridinecarboxylic acid ethyl ester (Aldrich, 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233 USA) in 100 ml of dichloromethane. After stirring the mixture for 36 hours, the precipitate was removed by filtration and the filtrate was evaporated. The residue was dissolved in ethyl acetate, washed successively with saturated aqueous sodium bisulfite solution (1×100 ml) and sodium bicarbonate solution (2×100 ml), dried (Na2SO4), and evaporated. The residue was purified by flash chromatography with an ethyl acetate-hexane eluant (5:95 to 100:0) to afford 8.1 g (33%) of the title compound as an oil. 1H NMR (CDCl3): δ 1.35 (3H, t, J=7), 4.36 (2H, q, J=7), 7.23-7.29 (1H, m), 7.61 (1H, d, J=7), 8.41 (1H, d, J=7).

Workup

  1. customremoving the solids
  2. filtrationby filtration
  3. customthe precipitate was removed by filtration
  4. customthe filtrate was evaporated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed successively with saturated aqueous sodium bisulfite solution (1×100 ml) and sodium bicarbonate solution (2×100 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was purified by flash chromatography with an ethyl acetate-hexane eluant (5:95 to 100:0)

Sources & evidence

ORD record
ord-73411b1ab73a4a659c4386e721793fc3
Source dataset
uspto-grants-1998_08
Patent number
US05789408

Reaction notes

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