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

HRID 44196

Reaktionsgleichung

Reaktionsgleichung von HRID 44196
[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][CH:25]=[N:24][CH:23]=1.Cl>C(O)C.O>[N:24]1[CH:25]=[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]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 91665PyroquilonHCID 6451240Aluminum(III) Chloride2×

Produkt 1

HCID 444798818-(Pyridine-3-carbonyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-oneAusbeute 22,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 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 nicotinoylchloride 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 ethanol gave the acylation product (624 mg, 2.24 mmol, 22%) as a yellow solid, mp (ethanol) 147° C. 1H-NMR (500 MHz, CDCl3): δ=2.72 (t, 3J=7.9 Hz, 2H), 3.02 (t, 3J=7.9 Hz, 2H), 3.23 (t, 3J=8.6 Hz, 2H), 4.14 (t, 3J=8.6 Hz, 2H), 7.44 (ddd, 3J=7.9 Hz, 3J=4.7 Hz, 5J=1.0 Hz, 1H), 7.53 (s, 1H), 7.58 (s, 1H), 8.06 (m, 1H), 8.78 (dd, 3J=5.0 Hz, 4J=1.9 Hz, 1H), 8.92 (dd, 4J=1.9 Hz, 5J=0.8 Hz, 1H). 13C-NMR (125 MHz, CDCl3): δ=24.2, 27.3, 31.4, 45.8, 199.9, 123.4, 126.1, 128.9, 129.4, 132.3, 134.0, 137.0, 146.1, 150.4, 152.4, 167.8, 193.6. MS m/z 278.79 (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 ethanol

Quellen und Nachweise

ORD-Eintrag
ord-65f42044164a4c2e93c4763e6f251c5c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541404B2

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