Ethanol → 2-[3-Chloro-4-(4-aminopyrazol-1-yl)phenyl]propionic acid

HRID 1733021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1733021
C(/[O-])=C(\[N+]([O-])=O)/C=O.O.[Na+].C(O)C.[Cl:14][C:15]1[CH:16]=[C:17]([CH:29]([CH3:33])[C:30]([OH:32])=[O:31])[CH:18]=[CH:19][C:20]=1[N:21]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[N:22]1.O>C(O)(=O)C.[Fe]>[Cl:14][C:15]1[CH:16]=[C:17]([CH:29]([CH3:33])[C:30]([OH:32])=[O:31])[CH:18]=[CH:19][C:20]=1[N:21]1[CH:25]=[C:24]([NH2:26])[CH:23]=[N:22]1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 962WaterHCID 12244252sodium N-oxido-1,3-dioxopropanimine oxide hydrateHCID 203035672-[3-Chloro-4-(4-nitropyrazol-1-yl)phenyl]propionic acid

Produkt 1

HCID 203035462-[3-Chloro-4-(4-aminopyrazol-1-yl)phenyl]propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The starting compound is obtained in the following manner: 22.8 g (59 mmoles) of 2-(3-chloro-4-hydraziniumphenyl)propionic acid p-toluenesulphonate and 9.8 g (64 mmoles) of sodium nitromalondialdehyde monohydrate are heated under reflux for 30 minutes in 180 ml of 80% strength ethanol. Concentration is then effected, followed by taking up with sodium bicarbonate and extraction with ether. The aqueous solution is acidified and extracted with ether. Through concentration of the ethereal phase there is obtained, after recrystallisation from ethanol, 2-[3-chloro-4-(4-nitropyrazol-1-yl)phenyl]propionic acid (m.p. 173°-173.5° C.). 5 g (16.9 mmoles) of 2-[3-chloro-4-(4-nitropyrazol-1-yl)phenyl]propionic acid are dissolved in 30 ml of glacial acetic acid, heated to 80° C.; portionwise, 3.8 g of iron powder and then 7 ml of water are added. After one hour, pouring on to ice is effected, followed by extraction with ether. The ether phase is dried, clarified with Tonsil, and concentrated. 2-[3-chloro-4-(4-aminopyrazol-1-yl)phenyl]propionic acid is obtained as oil [RF =0.25 (silica gel; CHCl3 /ethanol 4:1)].

Aufarbeitung

  1. customThe starting compound is obtained in the following manner
  2. concentrationConcentration
  3. extractionby taking up with sodium bicarbonate and extraction with ether
  4. extractionextracted with ether
  5. customThrough concentration of the ethereal phase there is obtained
  6. customafter recrystallisation from ethanol, 2-[3-chloro-4-(4-nitropyrazol-1-yl)phenyl]propionic acid (m.p. 173°-173.5° C.)
  7. additionpouring on to ice
  8. extractionfollowed by extraction with ether
  9. dry with materialThe ether phase is dried
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a09fd50d4c71433db1a98fd8420d4923
Quelldatensatz
uspto-grants-1980_12
Patentnummer
US04239901

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