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 521418Notes

Reaction equation

HRID 521418 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 89657238Methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate hydrobromideYield 65.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-7021bedf28204cc9b63209ef73a65e68
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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