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

HRID 1600749Notes

Reaction equation

HRID 1600749 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): 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-8e740866ef254452aee68272c2a04fc7
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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