Nipecotic Acid → 4-(2-Methyl-2-phenylhydrazinyl)-5,6-dihydropyridin-2(1H)-one

HRID 1614291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614291
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3](C(O)=O)[CH2:2]1.S(O)(O)(=O)=O.[CH3:15][N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:17].[OH-:24].[Na+]>O.Cl>[CH3:15][N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:17][C:4]1[CH2:3][CH2:2][NH:1][C:6](=[O:24])[CH:5]=1

Komponenten

6

Edukt 3

HCID 4498Nipecotic AcidHCID 14798Sodium HydroxideHCID 438107261-Methyl-1-phenylhydrazine sulfate

Produkt 1

HCID 108569264-(2-Methyl-2-phenylhydrazinyl)-5,6-dihydropyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

A mixture of 3-piperidinecarboxylic acid, 2,4-dioxo-, methyl ester (10.0 g) in industrial methylated spirits and water (1:1) (50 ml) and 5M aqueous hydrochloric acid (0.4 ml) was heated at 50°-55° for 30 min, and then heated at reflux for 1.5 h. The resulting mixture was cooled to room temperature and treated with 1-methyl-1-phenylhydrazine sulphate (2:1) (9.9 g) and 5M aqueous sodium hydroxide (11.6 ml). Water (5.5 ml) was added, and more water (33 ml) was added slowly over 45 min. The resultant solid was filtered off, washed with water (3×8 ml) and dried in vacuo at 43° to give the title compound (10.7 g), m.p. 180°-181°.

Aufarbeitung

  1. temperaturewas heated at 50°-55° for 30 min
  2. temperatureheated
  3. temperatureat reflux for 1.5 h
  4. filtrationThe resultant solid was filtered off
  5. washwashed with water (3×8 ml)
  6. customdried in vacuo at 43°

Quellen und Nachweise

ORD-Eintrag
ord-0d5bd5d1023e4f87a5de63cb94568458
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05196534

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