6-nitro-3-(N-propionyl-N-n-propylamino)chroman → 6-amino-3-(N-propionyl-N-n-propylamino)chroman

HRID 2210918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2210918
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH:8]([N:14]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[CH2:7]2)([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH:8]([N:14]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[CH2:7]2

Komponenten

4

Edukt 1

HCID 108511876-nitro-3-(N-propionyl-N-n-propylamino)chroman

Produkt 1

HCID 105634506-amino-3-(N-propionyl-N-n-propylamino)chromanAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 6-nitro-3-(N-propionyl-N-n-propylamino)chroman (17) (700 mg, 2.40 mmol) in glacial acetic acid (50 ml) was treated with zinc dust (1.0 g). The mixture was stirred at 50° C. for 90 minutes. The solution was filtered and acetic acid evaporated at reduced pressure. The product was dissolved in CH2Cl2 and washed with 5%-aqueous Na2CO3. The organic layer was separated, dried (Na2SO4) and the solvent was evaporated. The crude product was chromatographed on silica (60 g), with CH2Cl2 -CH3OH (19:1) as eluant, yielding 350 mg (56%) of 6-amino-3-(N-propionyl-N-n-propylamino)chroman (18) as an oil.

Aufarbeitung

  1. filtrationThe solution was filtered
  2. customacetic acid evaporated at reduced pressure
  3. dissolutionThe product was dissolved in CH2Cl2
  4. washwashed with 5%-aqueous Na2CO3
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was evaporated
  8. customThe crude product was chromatographed on silica (60 g), with CH2Cl2 -CH3OH (19:1) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-34bcc2ca02714362bdc7b98a59504fa4
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05461061

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