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

HRID 48207Notes

Reaction equation

HRID 48207 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5]([NH2:13])=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2.[C:15](O)(=[O:19])[C:16](O)=[O:17]>Cl>[Br:1][C:2]1[C:11]2[CH2:10][N:9]([CH3:12])[CH2:8][CH2:7][C:6]=2[C:5]2[NH:13][C:15](=[O:19])[C:16](=[O:17])[NH:14][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 103550328-Bromo-1,2,3,4-tetrahydro-2-methyl-5,6-isoquinolinediamine

Product 1

HCID 98181346-Bromo-8-methyl-1,4,7,8,9,10-hexahydro-pyrido[4,3-f]quinoxaline-2,3-dioneYield 24.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of the product from Example 13 (0.62 g, 2.56 mmol) and oxalic acid (0.23 g, 2.56 mmol) in 25 mL of 3N aqueous HCl solution were heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and the solid which formed was collected by filtration and washed with cold water. The solid was recrystallized from hot water and dried under vacuum (100° C., P2O5) to give the title compound as a tan solid (0.191 g, 20%), mp=315-320° C. (dec.).

Workup

  1. temperatureat reflux for 18 hours
  2. customthe solid which formed
  3. filtrationwas collected by filtration
  4. washwashed with cold water
  5. customThe solid was recrystallized from hot water
  6. dry with materialdried under vacuum (100° C., P2O5)

Sources & evidence

ORD record
ord-28485785eeb5490989bcf2076b9474c3
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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