4-Nitrophenol → HCID 59597003, compound

HRID 2265607Notes

Reaction equation

HRID 2265607 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)([O-:16])=[O:15].C(OCC)(=O)C.[OH-].[Na+]>ClC1C=CC=CC=1>[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH:3]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 9804-Nitrophenol2×HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59596919Isopropyl 4-Chloropicolinate

Product 1

HCID 59597003HCID 59597003, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

2-Propyl 4-chloropyridine-2-carboxylate (3.13 g) was dissolved in chlorobenzene (9.5 ml). 4-Nitrophenol (3.28 g) was added thereto, followed by stirring at 120° C. for 23 hr. 4-Nitrophenol (1.09 g) was added thereto, followed by stirring at 120° C. for 3 hr. The reaction mixture was allowed to cool down to room temperature. Ethyl acetate (50 ml) and a 1N aqueous solution of sodium hydroxide (50 ml) were added to the reaction mixture and stirred. Insoluble matter was precipitated, which was dissolved by addition of THF (50 ml). The organic layer was separated, washed with a 1N aqueous solution of sodium hydroxide (50 ml×3) and brine (50 ml) in this order, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=2:1 to 1:1). Fractions containing the target compound were concentrated under reduced pressure, and dried under reduced pressure to provide the titled compound as pale brown crystals (2.147 g, 45%).

Workup

  1. stirringby stirring at 120° C. for 3 hr
  2. temperatureto cool down to room temperature
  3. stirringstirred
  4. customInsoluble matter was precipitated
  5. dissolutionwhich was dissolved by addition of THF (50 ml)
  6. customThe organic layer was separated
  7. washwashed with a 1N aqueous solution of sodium hydroxide (50 ml×3) and brine (50 ml) in this order
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationThe solvent was concentrated under reduced pressure
  10. customThe resultant residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=2:1 to 1:1)
  11. additionFractions containing the target compound
  12. concentrationwere concentrated under reduced pressure
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-3c8682cd95ae480483fbabcaefcaaf42
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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