Pyridine → HCID 86621576, compound

HRID 420164Notes

Reaction equation

HRID 420164 reaction equation
[O:1](S(C(F)(F)F)(=O)=O)[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].O[C:17]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][C:18]=1[O:31][CH3:32].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:32][O:31][C:18]1[CH:19]=[C:20]([CH:26]=[C:27]([N+:28]([O-:30])=[O:29])[C:17]=1[O:1][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 44203157Ethyl 4-hydroxy-3-methoxy-5-nitrobenzoate

Product 1

HCID 86621576HCID 86621576, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

17.7 ml of Tf2O was added to a solution of 16.8 g of ethyl 4-hydroxy-3-(methyloxy)-5-nitrobenzoate and 11.3 ml of pyridine in 500 ml of CHCl3 at 0° C. The mixture was stirred for 30 min, then washed successively with water, HClaq, and saturated NaHCO3aq, dried over Na2SO4, and concentrated. The residual solid was washed with a mixed solvent of CHCl3 and n-hexane to give a 22.0 g of the intended compound as a pale orange solid.

Workup

  1. washwashed successively with water, HClaq, and saturated NaHCO3aq
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. washThe residual solid was washed with a mixed solvent of CHCl3 and n-hexane

Sources & evidence

ORD record
ord-1b8803283ab648f5a48b1046df5cbbc5
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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