7-Chloro-6-fluoro-1,4-dihydro-5-nitro-2,3-quinoxalinedione → HCID 10849759, compound

HRID 1781042Notes

Reaction equation

HRID 1781042 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[C:4]([N+:14]([O-:16])=[O:15])[C:3]=1F.[CH3:18][O-:19].[Na+]>CS(C)=O.O.Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[C:4]([N+:14]([O-:16])=[O:15])[C:3]=1[O:19][CH3:18]

Participants

6

Reactant 2

HCID 99927297-Chloro-6-fluoro-1,4-dihydro-5-nitro-2,3-quinoxalinedioneHCID 10942334Sodium Methoxide

Product 1

HCID 10849759HCID 10849759, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 7-Chloro-6-fluoro-5-nitroquinoxaline-2(1H),3(4H)-dione (0.100 g, 0.385 mmol, as prepared above) in DMSO (1.0 mL) at room temperature, sodium methoxide (0.125 g, 2.31 mmol, Mallinckrodt) was added in one portion. The resulting dark red solution was stirred overnight at room temperature. It was then diluted with water (5.0 mL) and acidified with concentrated HCl (6 drops) to pH ~2. The precipitated solid was filtered, washed with water (5.0 mL), and dried under vacuum to obtain 0.116 g (110%) of pure (1H NMR) title compound as a yellow powder; m.p. darkens at 316° C.; 1H NMR (DMSO-d6): δ3.821 (s, 3H), 7.275 (s, 1H), 12.079 (s, 1H) 12.121 (s, 1H). The NMR also indicates the presence of DMSO (reaction solvent).

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water (5.0 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-bdab480f98884bfcb8fb5bb903a163a5
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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