Hydrochloric Acid → Myosmine

HRID 389163

Reaktionsgleichung

Reaktionsgleichung von HRID 389163
C([N:5]1[CH2:9][CH2:8][CH:7]([C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=2)C1=O)=CCC.Cl>O>[CH:15]1[CH:14]=[N:13][CH:12]=[C:11]([C:10]2[CH2:7][CH2:8][CH2:9][N:5]=2)[CH:16]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 681592951-(But-1-enyl)-3-nicotinoyl-pyrrolidin-2-one

Produkt 1

HCID 442649MyosmineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1-(but-1-enyl)-3-nicotinoylpyrrolidin-2-one (II), (40 g, 0.1639 mol), 50 ml water and 85 ml HCl were refluxed together for 12 hrs. The reaction mixture was cooled to room temperature, washed with 50 ml×2 ethyl acetate, further cooled to 0° C. and pH adjusted to >13 using NaOH. The reaction mixture was extracted with 100 ml×3 of dichloromethane and the extract dried over Na2SO4. After removing the solvent under reduced pressure, the crude solid obtained was purified by high vacuum distillation to give colorless solid myosmine (16.75 g, 70%). 1H NMR (CDCl3): δ 2.05 (2H, m), 2.94 (2H, t), 4.06 (2H, t), 7.34 (1H, dd), 8.18 (1H, dt), 8.64 (1H, dd), and 8.99 (1H, d). 13C-NMR (CDCl3): δ 170.56, 151.1, 149.1, 134.6, 130.0, 123.3, 61.5, 34.7, and 22.5. IR: 2961, 1620, and 1590 Cm−1.

Aufarbeitung

  1. temperaturewere refluxed together for 12 hrs
  2. washwashed with 50 ml×2 ethyl acetate
  3. temperaturefurther cooled to 0° C.
  4. extractionThe reaction mixture was extracted with 100 ml×3 of dichloromethane
  5. dry with materialthe extract dried over Na2SO4
  6. customAfter removing the solvent under reduced pressure
  7. customthe crude solid obtained
  8. distillationwas purified by high vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-03a560d3e5024da7a0de676794516825
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378110B1

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