Pyridine → HCID 67247801, compound

HRID 1190861Notes

Reaction equation

HRID 1190861 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=O)[CH:3]=1.Cl.NO.[N:21]1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(OCC)(=O)C.O.ClCCl.C(N(CC)CC)C.C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]2[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[N:21]2)[CH:3]=1

Participants

10

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 443297Hydroxyamine hydrochlorideHCID 67246324HCID 67246324, compound

Product 1

HCID 67247801HCID 67247801, compound

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

1.03 g of 2-(4-bromopyridin-2-yl)-1-p-tolylethanone obtained in step 13.1 are placed in a round-bottomed flask with 0.99 g (14.2 mmol) of hydroxylamine monohydrochloride, 3 mL (37 mmol) of pyridine and 100 mL of ethanol. The reaction medium is stirred overnight and then concentrated under reduced pressure. The residue obtained is then taken up in 200 mL of ethyl acetate and 200 mL of water. The organic phase is recovered, dried over sodium sulfate and then concentrated under reduced pressure. 1.10 g of compound are recovered and dissolved in a round-bottomed flask containing 0 660 mL (4.74 mmol) of triethylamine and 30 mL of dichloromethane. The reaction medium is then cooled to about 5° C. and 0.200 mL (1.42 mmol) of trifluoroacetic anhydride is added dropwise. The medium is then stirred at room temperature for 3 hours, followed by hydrolysis with 100 mL of water. The medium is then stirred for 10 minutes, followed by filtration through a hydrophobic cartridge (Radleys® 70 mL liquid/liquid extraction column). 1.2 g of silica are then added to the filtrate, followed by concentrating under reduced pressure. The powder obtained is used as a solid deposit for a chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (95/5). 0.746 g (77%) of expected compound is recovered in the form of a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customThe organic phase is recovered
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custom1.10 g of compound are recovered
  7. dissolutiondissolved in a round-bottomed flask
  8. stirringThe medium is then stirred at room temperature for 3 hours
  9. stirringThe medium is then stirred for 10 minutes
  10. filtrationfollowed by filtration through a hydrophobic cartridge (Radleys® 70 mL liquid/liquid extraction column)
  11. addition1.2 g of silica are then added to the filtrate
  12. concentrationby concentrating under reduced pressure
  13. customThe powder obtained
  14. washeluting with a mixture of cyclohexane and ethyl acetate (95/5)
  15. custom0.746 g (77%) of expected compound is recovered in the form of a white powder

Sources & evidence

ORD record
ord-c0d21ced54d64420b0cb2b90e8d24fbe
Source dataset
uspto-grants-2014_03
Patent number
US08680096B2

Reaction notes

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