Hydrochloric Acid → 2-Amino-5-methoxy-4-(3-morpholinopropoxy)benzamide

HRID 1597212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1597212
Cl.[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:6][C:7]([N+:13]([O-])=O)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10]>CO.[Fe]>[NH2:13][C:7]1[CH:6]=[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:4]([O:3][CH3:2])=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 216992855-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide2×

Produkt 1

HCID 216992712-Amino-5-methoxy-4-(3-morpholinopropoxy)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Concentrated hydrochloric acid (30 ml) was added to a suspension of 5-methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide (5.67 g, 16.7 mmol) in methanol (150 ml) and the mixture was heated to 60° C. When the 5-methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide had dissolved, iron powder (5.6 g, 100 mmol) was added in portions to the reaction mixture which was then heated at 60° C. for 90 minutes. After cooling, the insolubles were removed by filtration through diatomaceous earth, the volatiles were removed from the filtrate by evaporation and the residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin colurnn, eluting with water and then with hydrochloric acid (pH2). Concentration of the fractions by evaporation gave a precipitate which was collected by filtration and dried under vacuum over phosphorus pentoxide to give 2-amino-5-methoxy4-(3-morpholinopropoxy)benzamide as a hydrochloride salt (4.67 g, 75%) as beige crystals.

Aufarbeitung

  1. temperaturewas then heated at 60° C. for 90 minutes
  2. temperatureAfter cooling
  3. customthe insolubles were removed by filtration through diatomaceous earth
  4. customthe volatiles were removed from the filtrate by evaporation
  5. customthe residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin colurnn
  6. washeluting with water
  7. customConcentration of the fractions by evaporation
  8. customgave a precipitate which
  9. filtrationwas collected by filtration
  10. dry with materialdried under vacuum over phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-92f5e21c8a0349ecb671cf74831e78b9
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294532B1

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