Ethanol → HCID 21324990, Verbindung

HRID 26189

Reaktionsgleichung

Reaktionsgleichung von HRID 26189
[CH2:1]([OH:3])[CH3:2].[CH3:4][O:5][C:6]1[C:7]([N+:17]([O-:19])=[O:18])=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2.Cl.[NH:21]1[CH2:26]CO[CH2:23][CH2:22]1.C(=O)([O-])O.[Na+]>O.C(OCC)C>[CH3:4][O:5][C:6]1[C:7]([N+:17]([O-:19])=[O:18])=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH:11]([CH2:26][N:21]1[CH2:22][CH2:23][O:3][CH2:1][CH2:2]1)[CH2:10][CH2:9]2

Komponenten

7

Edukt 4

HCID 702EthanolHCID 197884Morpholine, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 130673376-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-one

Produkt 1

HCID 21324990HCID 21324990, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In 100 ml. of ethanol is dissolved a mixture of 1 g. of 6-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone and 3 g. of morpholine hydrochloride and the mixed solution is reacted at 80° C. for 10 hours. The reaction mixture is cooled and, following addition of 500 ml. of water, it is shaken with 100 ml. of diethyl ether. The water layer is neutralized with sodium hydrogen carbonate and extracted with chloroform. The extract is dried and distilled under reduced pressure to remove the solvent. By the above procedure is obtained 6-methoxy-2-morpholinomethyl-5-nitro-3,4-dihydro-1(2H)-naphthalenone as an oily product. This product is dissolved in 50 ml. of methanol and, after addition of 1 g. of sodium borohydride, the solution is stirred at room temperature for 30 minutes. To this reaction mixture is added 500 ml. of water and the mixture is extracted with chloroform. The extract is dried and distilled under reduced pressure to remove the solvent. The above procedure provides an oil of 6-methoxy-2-morpholinomethyl-5-nitro-1,2,3,4-tetrahydro-1-naphthalenol. This product is dissolved in 20 ml. of ethanolic hydrochloric acid and the solution is heated at 80° C. for 1 hour. Following the addition of 50 ml. of ethyl acetate, the solution is cooled, whereupon 0.35 g. of 7-methoxy-3-morpholinomethyl-8-nitro-1,2-dihydronaphthalene hydrochloride is obtained as pale-yellow prisms melting at 200°-270° C. (gradually decomposed).

Aufarbeitung

  1. additiona mixture of 1 g
  2. temperatureThe reaction mixture is cooled
  3. additionaddition of 500 ml
  4. extractionextracted with chloroform
  5. customThe extract is dried
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-eebd0246bce042a592c82726ed11085e
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148897

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