Hydrazine hydrate (1:1) → 3-Amino-4-hexylbenzoic acid morpholide

HRID 1598600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1598600
[CH2:1]([C:7]1[CH:20]=[CH:19][C:10]([C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][C:8]=1[N+:21]([O-])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.NN>C(O)C.[Pd]>[NH2:21][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][C:7]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:11]([N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)=[O:12]

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 540077734-Hexyl-3-nitrobenzoic acid morpholide

Produkt 1

HCID 539494553-Amino-4-hexylbenzoic acid morpholideAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The compound ([5]-(54)-75) (700 mg) prepared in Example 62 was dissolved in ethanol (35 ml). After the solution was heated to 50° C., a suspension of 10% Pd/C (70 mg) in ethanol was added, and hydrazine monohydrate (0.35 ml) was added to the solution. The solution was stirred at 50° C. for 30 minutes. After the reaction was completed, the solution was filtered through celite 545 to remove the catalyst. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Kieselgel 60=20 g, ethyl acetate) to obtain the above-captioned compound ([5]-(55)-75) (631 mg) as colorless oil.

Aufarbeitung

  1. additionwas added
  2. filtrationthe solution was filtered through celite 545
  3. customto remove the catalyst
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Kieselgel 60=20 g, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-40f619676dff4338840c1502cbd8e574
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739131

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