Hydrochloric Acid → 7-Fluoro-6-ethoxy-5-nitro-1,4-dihydroquinoxaline-2,3-dione

HRID 1068620Notes

Reaction equation

HRID 1068620 reaction equation
F[C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[NH:8][C:7](=[O:13])[C:6](=[O:14])[NH:5]2.[O-:18][CH2:19][CH3:20].[Na+].Cl>O>[F:12][C:11]1[CH:10]=[C:9]2[C:4]([NH:5][C:6](=[O:14])[C:7](=[O:13])[NH:8]2)=[C:3]([N+:15]([O-:17])=[O:16])[C:2]=1[O:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 108002536,7-Difluoro-5-nitro-1,4-dihydro-2,3-quinoxalinedione

Product 1

HCID 107070597-Fluoro-6-ethoxy-5-nitro-1,4-dihydroquinoxaline-2,3-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 24 mg (0.098 mmol) of 6,7difluoro-5-nitro-1,4-dihydroquinoxaline-2,3-dione and 24 mg (0.33 mmol) of sodium ethoxide (96%) in 0.5 mL of DMSO-d6 was kept at room temperature for 5 h. The red solution was added to 3 mL of water and acidified with 2 N HCl to pH =4. The precipitate was filtered, washed with water, and dried to leave a yellow solid (24 mg, 91%); mp 293-295° C.; 1H NMR (DMSO-d6), 1.239 (t, 3, J=7.0), 4.141 (q, 2, J=7.2), 7.152 (1, d, J=11.7), 11.975 (s, 1), 12.135 (s, 1). 19F NMR, −134.06 (mb). MS, 269 (M+, 90), 241 (100), 195 (70). HRMS, Calcd for C10H8FN3O5269.0443, found 269.0454.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-9bb6caf12d694bf1864a732ab3f17086
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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