Hydrochloric Acid → 2-Amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochloride

HRID 1386300

Reaktionsgleichung

Reaktionsgleichung von HRID 1386300
[ClH:1].[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][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]>[ClH:1].[NH2:13][C:7]1[CH:6]=[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][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 218748225-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide

Produkt 1

HCID 218748202-Amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochlorideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Concentrated hydrochloric acid (5 ml) was added to a suspension of 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide (1.5 g, 4.64 mmol) in methanol (20 ml) and the mixture was heated at 50° C. to give a solution. Iron powder (1.3 g, 23.2 mmol) was added in portions and the reaction mixture was then heated at reflux for 1 hour. The mixture was allowed to cool, the insolubles were removed by filtration through diatomaceous earth and the volatiles were removed from the filtrate by evaporation. The residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with water and then with dilute hydrochloric acid (pH2). The fractions containing product were concentrated by evaporation and the resulting precipitate was collected by filtration and dried under vacuum over phosphorus pentoxide to give 2-amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochloride (1.44 g, 85%).

Aufarbeitung

  1. customto give a solution
  2. temperaturethe reaction mixture was then heated
  3. temperatureat reflux for 1 hour
  4. temperatureto cool
  5. customthe insolubles were removed by filtration through diatomaceous earth
  6. customthe volatiles were removed from the filtrate by evaporation
  7. customThe residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  8. washeluting with water
  9. additionThe fractions containing product
  10. concentrationwere concentrated by evaporation
  11. filtrationthe resulting precipitate was collected by filtration
  12. dry with materialdried under vacuum over phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-64b4e027b9d14f84b7f6da280335382d
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265411B1

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