Hydrochloric Acid → 8-(Pyridine-4-carbonyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one

HRID 2358974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2358974
[Al+3].[Cl-].[Cl-].[Cl-].[Na+].[Cl-].[CH2:7]1[C:17]2=[C:18]3[C:13](=[CH:14][CH:15]=[CH:16]2)[CH2:12][CH2:11][C:10](=[O:19])[N:9]3[CH2:8]1.Cl.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.Cl>CC(C)=O.O>[N:25]1[CH:26]=[CH:27][C:22]([C:21]([C:15]2[CH:14]=[C:13]3[C:18]4=[C:17]([CH2:7][CH2:8][N:9]4[C:10](=[O:19])[CH2:11][CH2:12]3)[CH:16]=2)=[O:28])=[CH:23][CH:24]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 91665PyroquilonHCID 6451240Aluminum(III) Chloride2×HCID 12262826Isonicotinoyl chloride hydrochloride

Produkt 1

HCID 444798808-(Pyridine-4-carbonyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-oneAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a molten mixture of AlCl3 (8.0 g, 60.0 mmol) and NaCl (2.34 g, 40.0 mmol) at 150° C. was added 1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one (1.79 g, 10.0 mmol) and thereafter isonicotinoylchloride hydrochloride salt (1.96 g, 11.0 mmol) portionwise. After stirring for 15 min and cooling to room temperature, excess aluminum chloride was decomposed by the addition of a chilled mixture of 10 ml concentrated hydrochloric acid and 200 ml water. Neutralization with NaHCO3 solution and subsequent extraction with ethyl acetate (3×100 ml), followed by drying over MgSO4 and removal of the solvent gave the crude product. Purification by crystallization from acetone gave the acylation product (751 mg, 2.70 mmol, 27%) as a yellow solid, mp (acetone) 184° C. 1H-NMR (500 MHz, CDCl3): δ=2.70 (t, 3J=7.7 Hz, 2H), 2.99 (t, 3J=7.8 Hz, 2H), 3.21 (t, 3J=8.2 Hz, 2H), 4.12 (t, 3J=8.2 Hz, 2H), 7.49 (m, 3H), 7.55 (s, 1H), 8.76 (d, 3J=5.1 Hz, 2H). 13C-NMR (125 MHz, CDCl3): δ=24.1, 27.2, 31.3, 45.7, 119.9, 122.6, 126.1, 129.0, 129.4, 131.4, 145.3, 146.3, 150.2, 167.8, 193.9. MS m/z 279.07 (MH+).

Aufarbeitung

  1. extractionNeutralization with NaHCO3 solution and subsequent extraction with ethyl acetate (3×100 ml)
  2. dry with materialby drying over MgSO4 and removal of the solvent
  3. customgave the crude product
  4. customPurification
  5. customby crystallization from acetone

Quellen und Nachweise

ORD-Eintrag
ord-c1bbbf804fa243eda143b3d618ba1bf1
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685960B2

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