Hydrochloric Acid → HCID 136092328, compound

HRID 1857437Notes

Reaction equation

HRID 1857437 reaction equation
C([O:4][C:5]1[C:6]2[C:11]([CH:12]=[C:13]([O:18][CH2:19]C)[C:14]=1[O:15][CH2:16]C)=[N:10][C:9](=[O:21])[C:8](=[O:22])[N:7]=2)(=O)C.[OH-].[Na+].Cl>O>[OH:4][C:5]1[C:6]2[C:11]([CH:12]=[C:13]([O:18][CH3:19])[C:14]=1[O:15][CH3:16])=[N:10][C:9](=[O:21])[C:8](=[O:22])[N:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22129639HCID 22129639, compound

Product 1

HCID 136092328HCID 136092328, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Acetyloxy-6,7-dimethoxy-2,3-quinoxalinedione (47) (30 mg, 0.107 mmol) was added to a single-necked 15-mL flask. Sodium hydroxide aqueous solution (2 N, 1 mL) was added to the flask under nitrogen with stirring. The solution was then stirred at room temperature for 24 h. The solution was diluted with water (3 mL) and then acidified with HCl (4 N, 1 mL) to pH=2 to give a brown solid, which was collected by filtration and dried in vacuo, giving 23 mg (86%) of the title compound; mp 285-286° C. (dec); 1H NMR (DMSO-d6, 300 MHz) δ 3.688 (s, 3 H), 3.694 (s, 3 H), 6.227 (s, 1 H), 9.769 (s, 1 H), 11.016 (s, 1 H), 11.658 (s, 1 H). EIMS m/e 238 (100, M+), HPLC purity>96%.

Workup

  1. stirringThe solution was then stirred at room temperature for 24 h
  2. customto give a brown solid, which
  3. filtrationwas collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ae3494e73a38442eb9af452b8a3eedb2
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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