3-Hydrazinopyridine → Methyl 2-[5-(3-chlorophenyl)-3-methyl-1-(pyridin-3-yl)pyrazol-4-yl]acetate

HRID 888723

Reaktionsgleichung

Reaktionsgleichung von HRID 888723
[NH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)[NH2:2].[Cl:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([CH:15]([C:21](=O)[CH3:22])[CH2:16][C:17]([O:19][CH3:20])=[O:18])=O>C(O)C>[Cl:9][C:10]1[CH:11]=[C:12]([C:13]2[N:1]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=3)[N:2]=[C:21]([CH3:22])[C:15]=2[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:24]=[CH:25][CH:26]=1

Komponenten

4

Edukt 2

HCID 109095193-HydrazinopyridineHCID 44247886Methyl 3-(3-chlorobenzoyl)-4-oxopentanoate

Produkt 1

HCID 24853498Methyl 2-[5-(3-chlorophenyl)-3-methyl-1-(pyridin-3-yl)pyrazol-4-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

0.577 g (4.233 mmol) of 3-hydrazinopyridine in 5.00 ml of ethanol was added to 0.650 g (2.419 mmol) of methyl 3-(3-chlorobenzoyl)-4-oxopentanoate, and the mixture was stirred in a closed vessel in a microwave oven at 130° C. for 1.5 h. The solvent was removed under reduced pressure, and the residue was taken up in dichloromethane and washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. Chromatography of the residue gave 0.364 g (42% of theory) of a light-yellow oil. 1H-NMR (CDCl3): see Table 2.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. washwashed twice with in each case 25 ml of water
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customChromatography of the residue gave 0.364 g (42% of theory) of a light-yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-76739736b14c447e83fa235c27e92d13
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252723B2

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