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

HRID 1068632Notes

Reaction equation

HRID 1068632 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 port. The resulting dark red solution was stirred overnight at room temperate. 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): δ 3.821 (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-f772d43525684233bdf3ec91e313b1a3
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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