Hydrochloric Acid → HCID 86760946, compound

HRID 730048Notes

Reaction equation

HRID 730048 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[N:18]O)[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.Cl>CO.[Pd]>[ClH:1].[NH2:18][CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)[C:9]([C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1363357791-(2-Chloropyridin-4-yl)-2-(4-fluorophenyl)ethane-1,2-dione-1-oxime

Product 1

HCID 86760946HCID 86760946, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

With gentle heating, 22a (1.5 g; 5.4 mmol) was dissolved in methanol (15 ml). The solution was cooled to room temperature, HCl-containing methanol (20 ml) was added and the mixture was transferred into a two-necked flask. Pd—C 10% (150 mg) was introduced into the initial charge. The reaction vessel was evacuated using an oil pump, and H2 was then introduced via a gas inlet capillary (4×). At room temperature, the suspension was shaken in a closed three-necked flask under an atmosphere of H2 (240 strokes/min) until no more starting material could be detected by thin-layer chromatography (6 h). The suspension was filtered and the catalyst was washed with plenty of methanol. The combined filtrate was concentrated and the mustard-colored solid-amorphous residue was dried using an oil pump. The crude product was used without further purification for the next reaction step.

Workup

  1. additionwas added
  2. customthe mixture was transferred into a two-necked flask
  3. additioninitial charge
  4. customThe reaction vessel was evacuated
  5. additionwas then introduced via a gas inlet capillary (4×)
  6. customcould be detected by thin-layer chromatography (6 h)
  7. filtrationThe suspension was filtered
  8. washthe catalyst was washed with plenty of methanol
  9. concentrationThe combined filtrate was concentrated
  10. customthe mustard-colored solid-amorphous residue was dried
  11. customThe crude product was used without further purification for the next reaction step

Sources & evidence

ORD record
ord-03e67b17acf74eef872ca58154e409e3
Source dataset
uspto-grants-2009_09
Patent number
US07582660B2

Reaction notes

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