Benzylamine → HCID 19805536, Verbindung

HRID 1681696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1681696
[CH2:1]([NH:8][C:9](=[O:24])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][C:11]=1[N+:21]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C=CC(C(O)=O)=C([N+]([O-])=O)C=1.C(I)CCC.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].C(N)C1C=CC=CC=1>C(O)C.O.CN(C)C=O>[CH2:1]([N:8]1[C:9](=[O:24])[C:10]2[C:11](=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:14][CH:15]=2)[NH:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

10

Edukt 6

HCID 7504BenzylamineHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 19805467HCID 19805467, VerbindungHCID 217533454-Hydroxy-2-nitrobenzoic acid

Produkt 1

HCID 19805536HCID 19805536, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Using a similar procedure to that described in Example 34, but starting from N-benzyl-4-butoxy-2-nitrobenzamide [obtained as an oil of satisfactory purity by heating a mixture containing 4-hydroxy-2-nitrobenzoic acid (J.Chem.Soc., 1949, 1502), butyl iodide, potassium carbonate and N,N-dimethylformamide; hydrolysing a solution of the ester in ethanol with aqueous sodium hydroxide and coupling the resultant acid with benzylamine using the conditions described for the preparation of starting materials in Example 1], using a mixture of ethanol and water (3/1 v/v) as solvent and heating the reaction for 8 hours there was obtained 1,2-dihydro-2-benzyl-6-butoxy-3H-indazol-3-one as a solid, m.p. 148-149° C., in 27% yield.

Aufarbeitung

  1. customobtained as an oil of satisfactory purity
  2. temperatureby heating a mixture
  3. customdescribed for the preparation of starting materials in Example 1],
  4. temperatureheating
  5. customthe reaction for 8 hours there

Quellen und Nachweise

ORD-Eintrag
ord-573a227bcb8f40f390bce1e6b37de2da
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05173496

Notizen zur Reaktion

Wird geladen…