Oxalic acid dihydrate → HCID 15429089, compound

HRID 53803Notes

Reaction equation

HRID 53803 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([F:11])=[CH:4][C:3]=1[NH2:12].O.O.[C:15](O)(=[O:19])[C:16](O)=[O:17]>Cl>[F:11][C:5]1[CH:4]=[C:3]2[C:2]([NH:1][C:15](=[O:19])[C:16](=[O:17])[NH:12]2)=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 154290905-Fluoro-3-nitrobenzene-1,2-diamine

Product 1

HCID 15429089HCID 15429089, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1,2-diamino-4-fluoro-6-nitrobenzene (80 mg, 0.46 mmole) and oxalic acid dihydrate (70 mg, 0.56 mmole, used as received) in 4N HCl (4 mL) was refluxed at 120°-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the supernatant was removed. The yellow solid was washed by cold water (2×2 mL), collected by filtration, and dried in vacuo for 2 h, affording 45 mg of crude 7-fluoro-5-nitro-1,4-dihydro-2,3-quinoxalinedione (42% ) as a yellow powder. The crude product was taken up in 1N NaOH (1 mL) and filtered. The filtrate was acidified to pH=3, affording 35 mg of 7-fluoro-5-nitro-1,4-dihydro-2,3-quinoxalinedione (33% ), mp: 333°-335° C. (dec.), IR (KBr, cm-1): 3427, 3328, 3104, 3072, 1716, 1545. 1H NMR (DMSO-d6): δ 12.418 (s, 1H), 11.149(s, 1H), 7.819 (dd, J1 =2.4 Hz, J2 =9.0 Hz, 1H), 7.297 (dd, J1 =2.4 Hz, J2 =9.0 Hz, 1H); HRMS: calcd for C8H4FN3O4 (M+) m/z: 225.0185; found: 225.0188.

Workup

  1. temperaturewas refluxed at 120°-5° C. for 3 h
  2. customthe supernatant was removed
  3. washThe yellow solid was washed by cold water (2×2 mL)
  4. filtrationcollected by filtration
  5. customdried in vacuo for 2 h

Sources & evidence

ORD record
ord-1ec4b9762d60421babdc820d9f100bca
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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