Acetic Anhydride → HCID 18328986, Verbindung

HRID 1034256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1034256
[CH3:1][CH:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][NH:3]1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>[NH4+].[OH-].C(OCC)(=O)C>[CH3:1][CH:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][N:3]1[C:17](=[O:19])[CH3:18]

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 710282,3,4,9-Tetrahydro-6-methoxy-1-methyl-1H-pyrido(3,4-b)indole

Produkt 1

HCID 18328986HCID 18328986, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14923Ammonium HydroxideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 700 mg (3.24 mmol) 1-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline, and 5 drops NH4OH in ethyl acetate was added 0.4 mL (3.88 mmol) acetic anhydride under N2 gas. The reaction was stirred for 20 min. and then washed with water. The organic layer collected was dried over MgSO4, filtered, and concentrated in vacuo to a dark oil. The oil was dissolved in methanol and chromatographed on reverse phase C-18 using methanol and water. The product was collected and concentrated to a white solid, which showed characteristic peaks: NMR (CDCl3) δ: 1.45 ppm (d, 3H), 2.25 ppm (s, 3H), 3.85 ppm (s, 3H).

Aufarbeitung

  1. washwashed with water
  2. customThe organic layer collected
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a dark oil
  6. dissolutionThe oil was dissolved in methanol
  7. customchromatographed on reverse phase C-18
  8. customThe product was collected
  9. concentrationconcentrated to a white solid, which

Quellen und Nachweise

ORD-Eintrag
ord-36e5f3b52127447b84cfc08d4bcd774f
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05314908

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