Aluminium lithium hydride → 8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5,6-dihydro-dibenzo[c,h]1,6-naphthyridine

HRID 1825771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825771
[CH3:1][O:2][C:3]1[C:4]([O:31][CH3:32])=[CH:5][C:6]2[C:15]3[C:10](=[C:11]4[CH:19]=[C:18]5[O:20][CH2:21][O:22][C:17]5=[CH:16][C:12]4=[N:13][CH:14]=3)[N:9]([CH:23]([CH3:28])[CH2:24][N:25]([CH3:27])[CH3:26])[C:8](=O)[C:7]=2[CH:30]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[C:4]([O:31][CH3:32])=[CH:5][C:6]2[C:15]3[C:10](=[C:11]4[CH:19]=[C:18]5[O:20][CH2:21][O:22][C:17]5=[CH:16][C:12]4=[N:13][CH:14]=3)[N:9]([CH:23]([CH3:28])[CH2:24][N:25]([CH3:26])[CH3:27])[CH2:8][C:7]=2[CH:30]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 221394918,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5H-dibenzo [c,h]1,6-naphthyridin-6-one

Produkt 1

HCID 221395208,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5,6-dihydro-dibenzo[c,h]1,6-naphthyridineAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The title compound was prepared as follows. 8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-one (80 mg, 0.18 mmol; Example 7) in THF (150 mL) was added to LiAlH4 (50 mg, 1.3 mmol), and the mixture was stirred under nitrogen at reflux for 4h. The reaction was quenched by the sequential addition of water (5 drops), 10% NaOH (5 drops), and water (5 drops). The mixture was filtered through Celite and evaporated, and the crude mixture was chromatographed on silica in 1.0% methanol in chloroform to give 35 mg of the reduced product, in 45.4% yield; mp 153-154° C.; 1H NMR (CDCl3) δ 1.16 (d, 3H, J=8), 2.38 (dd, 2H, J=12.2, 8.0), 3.68-3.80 (m, 1), 3.88 (s, 3H), 4.24 (s, 2H), 6.16 (s, 2H), 6.64 (s, 1H), 7.24 (s, 1H), 7.40 (s, 2H), 7.62 (s, 1H), 8.88 (s, 1H); 13C NMR (CDCl3) δ: 17.7, 45.6, 46.0, 56.2, 56.4, 57.8, 64.2, 100.1, 101.7, 105.8, 106.4, 108.5, 120.5, 120.6, 123.6, 126.9, 143.4, 146.6, 147.7, 148.9, 149.5, 149.6, 150.0; HRMS calcd for C24H27N3O4H 422.2002; found 422.2081.

Aufarbeitung

  1. temperatureat reflux for 4h
  2. customThe reaction was quenched by the sequential addition of water (5 drops), 10% NaOH (5 drops), and water (5 drops)
  3. filtrationThe mixture was filtered through Celite
  4. customevaporated
  5. customthe crude mixture was chromatographed on silica in 1.0% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-480816443c7c47078005c563183e527e
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049315B2

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