Hydrochloric Acid → HCID 19827814, compound

HRID 1494345Notes

Reaction equation

HRID 1494345 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[N+:15]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[C:20](O)(=[O:24])[C:21](O)=[O:22].Cl>C(O)C.C(OCC)(=O)C.[Ni]>[CH:1]1([N:7]2[C:8]3[C:9](=[CH:10][C:11]([F:14])=[CH:12][CH:13]=3)[NH:15][C:21](=[O:22])[C:20]2=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 61373Oxalic acid dihydrateHCID 12793832HCID 12793832, compound

Product 1

HCID 19827814HCID 19827814, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2.0 g (8.4 mmol) N-cyclohexyl-4-fluoro-2-nitroaniline in a mixture of 100 ml ethanol and 50 ml ethyl acetate was hydrogenated at atm. pressure by using Ra-Ni (1 g) as a catalyst. The reaction mixture was filtered and evaporated in vacuo to give an oil. A mixture of the oil, 2.8 g (23 mmol) oxalic acid dihydrate, 10 ml ethanol and 150 ml 4N hydrochloric acid was refluxed for 11/2h. After cooling to 25° C. the precipitate was filtered off and washed with water to give 1.1 g (50%) 1-cyclohexyl-6-fluoroquinoxaline-2,3(1H,4H)-dione. M.p. 289.8° C., 1H-NMR (DMSO-d6): 12.0 (1H, broad s), 7.6 (1H, M), 7.0 (2H, M), 4.5 (1H, M), 2.6-0.9 (10H, M).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. customto give an oil
  4. temperaturewas refluxed for 11/2h
  5. filtrationwas filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-cde42b947da04dd3a9375fcd451c4319
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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