Sodium Hydroxide → 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 862566Notes

Reaction equation

HRID 862566 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20]C)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([OH:20])=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10066635Methyl 2-(9-bromo-2,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[1,2,3-de]quinoxalin-5-yl)acetate

Product 1

HCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9-bromo-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (25.0 g, 0.071 mol) in a mixture of THF (350 mL) and methanol (350 mL) was added aqueous 1N NaOH (440 mL). The mixture was stirred for 2 h at room temperature, concentrated to ca. 500 mL, and acidified by addition of aqueous 1N HCl. The precipitates formed were collected by filtration, washed with distilled water, and dried in vacuo to give 22.9 g of the title compound (95%).

Workup

  1. concentrationconcentrated to ca. 500 mL
  2. additionacidified by addition of aqueous 1N HCl
  3. customThe precipitates formed
  4. filtrationwere collected by filtration
  5. washwashed with distilled water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b5fd14df186749cf9174f254895e87d0
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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