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

HRID 1106426Notes

Reaction equation

HRID 1106426 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][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7]2.[C:21](O)(=[O:25])[C:22](O)=[O:23]>Cl>[Br:1][C:2]1[C:3]2[CH2:4][CH2:5][N:6]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:7][C:8]=2[C:9]2[NH:13][C:21](=[O:25])[C:22](=[O:23])[NH:12][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 155241895-Bromo-1,2,3,4-tetrahydro-2-(phenylmethyl)-7,8-isoquinolinediamine

Product 1

HCID 155241906-Bromo-1,4,7,8,9,10-hexahydro-9-(phenylmethyl)pyrido[3,4-f]quinoxaline-2,3-dioneYield 89%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of the product from Example 7 (0.64 g, 1.93 mmol) in 3N HCl (25 mL) was treated with oxalic acid (0.37 g, 2.9 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 (0.57 g, 89%) as a light brown solid, mp=297-302° C.

Workup

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

Sources & evidence

ORD record
ord-6b87b5aeaa6a49b2a322324572935068
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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