3,4-Dinitrophenol → HCID 17756075, compound

HRID 491611Notes

Reaction equation

HRID 491611 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].[CH3:14][NH:15][C:16]([C:18]1[CH:23]=[C:22](Cl)[CH:21]=[CH:20][N:19]=1)=[O:17]>C(Cl)Cl.[OH-].[Na+]>[CH3:14][NH:15][C:16]([C:18]1[CH:23]=[C:22]([O:13][C:6]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:21]=[CH:20][N:19]=1)=[O:17]

Participants

5

Reactant 2

HCID 113483,4-DinitrophenolHCID 14768144-Chloro-N-methylpicolinamide

Product 1

HCID 17756075HCID 17756075, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
170 °C

Procedure

3,4-Dinitrophenol (12.3 g, 66.8 mmol) and 4-chloro-pyridine-2-carboxylic acid methylamide prepared similarly as described in patent WO 00/42012 (less than 7.79 g, 45.7 mmol, due to contaminant) in an open 50 mL round-bottom flask provided with stir bar and fitted with running water condenser. The reaction was heated at 150° C. for 1 h and at 170° C. for 16 h. The reaction was cooled to RT and dissolved in CH2Cl2 and 2N NaOH (aq). The layers were separated, and the organic layer was washed with a mix of brine and 2 N NaOH. The aqueous layers were back-extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography using a hexanes-to-hexanes/EtOAc gradient, to yield the title compound.

Workup

  1. customas described in patent WO 00/42012 (less than 7.79 g, 45.7 mmol, due to contaminant) in an open 50 mL round-bottom flask
  2. customprovided
  3. customfitted with running water condenser
  4. temperatureThe reaction was cooled to RT
  5. customThe layers were separated
  6. washthe organic layer was washed with
  7. additiona mix of brine and 2 N NaOH
  8. extractionThe aqueous layers were back-extracted with CH2Cl2
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cb50a10f0fc749aab06c7bf8b636f038
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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