Hydrochloric Acid → Myosmine

HRID 1942951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942951
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. 1R: 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-796b0d68aa3745f389342c1234364b48
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389733B2

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