Hydrochloric Acid → HCID 66811089, compound

HRID 730049Notes

Reaction equation

HRID 730049 reaction equation
[F: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.C(O)(C)C.[ClH:24]>[Pd]>[ClH:24].[NH2:18][CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F: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 3

HCID 313Hydrochloric Acid2×HCID 3776IsopropanolHCID 1363357801-(2-Fluoropyridin-4-yl)-2-(4-fluorophenyl)ethane-1,2-dione-1-oxime

Product 1

HCID 66811089HCID 66811089, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

With gentle heating, 22b (5.0 g; 19 mmol) was dissolved in HCl-containing isopropanol (IsOH/HCl-saturated IsOH 1+1, 60 ml). The yellowish solution was cooled to room temperature and transferred into a two-necked flask (100 ml). Pd—C 10% (1.5 g) 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 (6.5 h). The catalyst was filtered off. The filtration residue was washed with plenty of methanol (about 800 ml). The combined filtrates were concentrated and the solid-amorphous residue was dried on an oil pump. The crude product was used without further purification for the next reaction step.

Workup

  1. customtransferred into a two-necked flask
  2. additioninitial charge
  3. customThe reaction vessel was evacuated
  4. additionwas then introduced via a gas inlet capillary (4×)
  5. customcould be detected by thin-layer chromatography (6.5 h)
  6. filtrationThe catalyst was filtered off
  7. washThe filtration residue was washed with plenty of methanol (about 800 ml)
  8. concentrationThe combined filtrates were concentrated
  9. customthe solid-amorphous residue was dried on an oil pump
  10. customThe crude product was used without further purification for the next reaction step

Sources & evidence

ORD record
ord-a5162a8ed09a4b7399d200a021efcd71
Source dataset
uspto-grants-2009_09
Patent number
US07582660B2

Reaction notes

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