Nitric Acid → 5-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride

HRID 454006

Reaktionsgleichung

Reaktionsgleichung von HRID 454006
[N+:1]([O-:4])(O)=[O:2].[ClH:5].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[C:11]([OH:13])=[O:12]>C(O)(C(F)(F)F)=O>[ClH:5].[CH3:6][O:7][C:8]1[C:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:15][C:14]([N+:1]([O-:4])=[O:2])=[C:10]([CH:9]=1)[C:11]([OH:13])=[O:12]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 248202363-Methoxy-4-[3-(1-pyrrolidinyl)propoxy]-benzoic acid Hydrochloride

Produkt 1

HCID 684411845-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochlorideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Fuming nitric acid (2.4 ml, 57.9 mmol) was added slowly at 0° C. to a solution of 3-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (12.15 g, 38.17 mmol) in TFA (40 ml). The cooling bath was removed and the reaction mixture stirred at ambient temperature for 1 hour. The TFA was removed by evaporation and ice/water was added to the residue and the solvent removed by evaporation. The solid residue was dissolved in dilute hydrochloric acid (pH2.2), poured onto a Diaion (trade mark of Mitsubishi) HP20SS resin column and eluted with methanol (gradient 0 to 50%) in water. Concentration of the fractions by evaporation gave a precipitate which was collected by filtration and dried under vacuum over phosphorus pentoxide to give 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (12.1 g, 90%).

Aufarbeitung

  1. customThe cooling bath was removed
  2. customThe TFA was removed by evaporation and ice/water
  3. additionwas added to the residue
  4. customthe solvent removed by evaporation
  5. dissolutionThe solid residue was dissolved in dilute hydrochloric acid (pH2.2)
  6. additionpoured onto a Diaion (trade mark of Mitsubishi) HP20SS resin column
  7. washeluted with methanol (gradient 0 to 50%) in water
  8. customConcentration of the fractions by evaporation
  9. customgave a precipitate which
  10. filtrationwas collected by filtration
  11. dry with materialdried under vacuum over phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-e5dec7581ee54344a9ee3da26fad4a2d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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