Oxalic Acid → 6-Bromo-1,4,7,8,9,10-hexahydro-9-(2-phenylethyl)pyrido[3,4-f]quinoxaline-2,3-dione

HRID 1530841Notes

Reaction equation

HRID 1530841 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([NH2:12])[C:9]([NH2:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:7]2.[C:22](O)(=[O:26])[C:23](O)=[O:24]>Cl>[Br:1][C:2]1[C:3]2[CH2:4][CH2:5][N:6]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:7][C:8]=2[C:9]2[NH:13][C:22](=[O:26])[C:23](=[O:24])[NH:12][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 155241925-Bromo-1,2,3,4-tetrahydro-2-(2-phenylethyl)-7,8-isoquinolinediamine

Product 1

HCID 155241936-Bromo-1,4,7,8,9,10-hexahydro-9-(2-phenylethyl)pyrido[3,4-f]quinoxaline-2,3-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of the product from Example 10 (0.54 g, 1.56 mmol) in 3N HCl (20 mL) was treated with oxalic acid (0.3 g, 2.34 mmol) and refluxed for four hours. When cool to room temperature the precipitate was filtered, suspended in water (70 mL) and basifyed to pH 10. The solids were filtered, and dried to give the title compound (0.37 g, 60%) as a brown solid, mp=290-295° C.

Workup

  1. temperaturerefluxed for four hours
  2. filtrationwas filtered
  3. filtrationThe solids were filtered
  4. customdried

Sources & evidence

ORD record
ord-9a2009b991e44cad9973b61da79d0920
Source dataset
uspto-grants-2001_03
Patent number
US06197771B1

Reaction notes

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