Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate → Methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate hydrobromide

HRID 521418

Reaktionsgleichung

Reaktionsgleichung von HRID 521418
C([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[C:18]([Br:26])=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]=3[C:12](=[O:27])[C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[BrH:26].[O:27]=[C:12]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:17][C:16]=2[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]1=2

Komponenten

5

Edukt 2

HCID 89657401Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 89657238Methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate hydrobromideAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (6.6 g, 15.4 mmol) in MeOH (100 mL) was added Pd/C (3.0 g, 5%, 50% water), the mixture was stirred at atmosphere of hydrogen for about 6.0 h. Then the mixture was filtered, washed with MeOH (20 mL). The filtrate was concentrated and the residue was recrystallized with MeOH (2.5 mL) to afford the product (3.4 g, 65%) as a white solid. 1H NMR (DMSO-d6) δ 12.0 (s, 1H), 9.18 (s, 1H), 7.61-7.72 (m, 2H), 7.22-7.23 (m, 1H), 4.32 (s, 2H), 3.81 (s, 3H), 3.38-3.40 (m, 2H), and 2.66-2.67 (m, 2H).

Aufarbeitung

  1. filtrationThen the mixture was filtered
  2. washwashed with MeOH (20 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized with MeOH (2.5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-7021bedf28204cc9b63209ef73a65e68
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328111B2

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