Hydrochloric Acid → HCID 19748915, Verbindung

HRID 414179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414179
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]=1.C(N(CC)[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][C:28]=1[CH3:33])C.[ClH:37].[NH4+].[OH-]>O1CCCC1.O>[ClH:37].[CH:21]1[C:22]2[CH:13]3[N:14]([C:26](=[O:34])[C:27]4[CH:32]=[CH:31][CH:30]=[N:29][C:28]=4[CH2:33]3)[CH2:15][CH2:16][C:17]=2[CH:18]=[CH:19][CH:20]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 14923Ammonium HydroxideHCID 767053,4-DihydroisoquinolineHCID 14307657N,N-Diethyl-2-methylpyridine-3-carboxamideHCID 178418339Butyllithium

Produkt 1

HCID 19748915HCID 19748915, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

Diisopropylamine (28 ml) and 150 ml of tetrahydrofuran were cooled to -65° C. and 125 mL of 1.6M n-butyllithium was added. To the resulting solution was added a solution of 16.2 g of 3,4-dihydroisoquinoline and 38.4 g of 2-methylnicotinic acid diethylamide in tetrahydrofuran. The mixture was allowed to warm to -20° C. and 600 ml of 3N hydrochloric acid was then added followed by 200 ml of water. The mixture was basified with NH4OH and extracted twice with ether. The ether extracts were combined, dried over anhydrous magnesium sulfate and evaporated to a residue, which was dissolved in methanol and acidified with anhydrous HCl in ether. Acetone (50 ml) was added and the mixture was allowed to stand overnight. The crystalline product was collected by filtration, yielding 34 g of (±)-5,6,13,13a-tetrahydroisoquino[2,1-g][1,6]naphthyridine-8-one hydrochloride, m.p. 220°-222° C.

Aufarbeitung

  1. extractionextracted twice with ether
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated to a residue, which
  4. dissolutionwas dissolved in methanol
  5. additionAcetone (50 ml) was added
  6. filtrationThe crystalline product was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-cf607da1e3d246d0a51e3764a439762d
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791108

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