Sodium Hydroxide → HCID 178435013, compound

HRID 1729974Notes

Reaction equation

HRID 1729974 reaction equation
C([C:4]1[C:13]([CH2:14][O:15][C:16](=[O:18])[CH3:17])=[N+:12]([O-:19])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]=1[O-:20])(=O)C.[OH-].[Na+]>C(Cl)Cl>[OH:18][C:16]1([CH3:17])[C:4]2=[N+:5]([O-:20])[C:6]3[C:11]([N+:12]([O-:19])=[C:13]2[CH2:14][O:15]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178475863HCID 178475863, compound

Product 1

HCID 178435013HCID 178435013, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Acetyl-3-acetoxymethylquinoxaline 1,4-dioxide (2.0 g., 7.24 mmol.) was dissolved in ice-cold concentrated hydrochloric acid (9 ml.). The reaction mixture was allowed to warm to room temperature and was stirred for 3 hours. Methylene chloride (20 ml.) was added, and the two-phase system was cooled in an ice-bath and made slightly basic (pH 8) with 50% sodium hydroxide solution. The methylene chloride layer was separated and the aqueous layer was extracted with more methylene chloride (two 20-ml. portions). The combined methylene chloride extracts were treated with activated carbon and evaporated under reduced pressure leaving a yellow solid. Recrystallization from methanol gave a 310 mg. (18% yield) of 1-hydroxy-1-methyl-1,3-dihydrofuro[3,4-b]quinoxaline 4,9-dioxide having m.p. 163°-165° C.

Workup

  1. temperaturethe two-phase system was cooled in an ice-bath
  2. customThe methylene chloride layer was separated
  3. extractionthe aqueous layer was extracted with more methylene chloride (two 20-ml. portions)
  4. additionThe combined methylene chloride extracts were treated with activated carbon
  5. customevaporated under reduced pressure
  6. customleaving a yellow solid
  7. customRecrystallization from methanol
  8. customgave a 310 mg

Sources & evidence

ORD record
ord-69e74184952f4adb9cdc787015c647ea
Source dataset
uspto-grants-1976_11
Patent number
US03991053

Reaction notes

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