Hydrochloric Acid → HCID 136092327, compound

HRID 1857436Notes

Reaction equation

HRID 1857436 reaction equation
C[O:2][C:3]1[C:12]([O:13]C)=[CH:11][C:10]2[C:5](=[N:6][C:7](=[O:16])[C:8](=[O:15])[N:9]=2)[CH:4]=1.B(Br)(Br)Br.[OH-].[Na+].Cl>C(Cl)Cl>[OH:2][C:3]1[C:12]([OH:13])=[CH:11][C:10]2[C:5](=[N:6][C:7](=[O:16])[C:8](=[O:15])[N:9]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 21189996HCID 21189996, compound

Product 1

HCID 136092327HCID 136092327, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 6,7-dimethoxy-2,3-quinoxalinedione (45) (222 mg, 1.0 mmol) in 2 mL of methylene dichloride was added 5 mL of a solution of boron tribromide in methylene dichloride (1 M, Aldrich). The resulting mixture was stirred at room temperature for 24 hr. The mixture was then poured into ice-water (10 g) to form a suspension. Aquous sodium hydroxide (20%, 10 mL) was added to the suspension to form a red solution. The solution was acidified with 6 N HCl (10 mL) to pH=1. The suspension was centrifuged, washed with methanol, and dried in vacuo, giving 170 mg (88%) of the product as a brown solid; mp>350° C.; 1H NMR (DMSO-d6, 300 MHz) δ 6.541 (s, 2 H), 8.989 (s, 2 H), 11.543 (s, 2 H). EIMS m/e 194 (100, M+). (HPLC>99%).

Workup

  1. customto form a suspension
  2. customto form a red solution
  3. washwashed with methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0904ce1e5e3e43e89daf8f592a66d0c3
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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