5-Bromo-8-ethoxalylamino-7-nitroquinoline → 1,4,7,8,9,10-Hexahydro-pyrido[2,3-f]quinoxaline-2,3-dione

HRID 48231Notes

Reaction equation

HRID 48231 reaction equation
C([O:3][C:4](=O)[C:5]([NH:7][C:8]1[C:9]([N+:19]([O-])=O)=[CH:10][C:11](Br)=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)=[O:6])C.[H][H]>C(O)(=O)C.[Pd]>[NH:7]1[C:8]2[C:17]3[NH:16][CH2:15][CH2:14][CH2:13][C:12]=3[CH:11]=[CH:10][C:9]=2[NH:19][C:4](=[O:3])[C:5]1=[O:6]

Participants

5

Reactant 2

HCID 117264985-Bromo-8-ethoxalylamino-7-nitroquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 118206471,4,7,8,9,10-Hexahydro-pyrido[2,3-f]quinoxaline-2,3-dioneYield 44.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of the product from Example 83 (1 g, 2.7 mmol) in 250 mL acetic acid was treated with 20% Pd/C (0.1 g) and shaken on a Parr apparatus under 52 psi hydrogen gas for 21 hours. After removal of the catalyst, the solvent was evaporated but gave negligible material. The catalyst/celite was washed two times with 1 N HCl, and the aqueous solution was basified with sodium bicarbonate. The precipitate was collected by filtration, dried and then recrystallized from methanol/dimethylformamide to give the title compound (0.26 g, 44% yield) mp>300° C.

Workup

  1. customAfter removal of the catalyst
  2. customthe solvent was evaporated
  3. customgave negligible material
  4. washThe catalyst/celite was washed two times with 1 N HCl
  5. filtrationThe precipitate was collected by filtration
  6. customdried
  7. customrecrystallized from methanol/dimethylformamide

Sources & evidence

ORD record
ord-53b4c64284844d0e9ceff9418e683dc7
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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