Hydrochloric Acid → HCID 19827791, compound

HRID 1494340Notes

Reaction equation

HRID 1494340 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[C:19]([OH:24])(=O)[C:20](O)=[O:21].[ClH:25]>C(O)C.C(OC(=O)C)C.[Ni]>[CH:1]1([N:7]2[C:8]3[C:9](=[CH:10][CH:11]=[C:12]([Cl:25])[CH:13]=3)[NH:14][C:20](=[O:21])[C:19]2=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 61373Oxalic acid dihydrateHCID 3101179N-cyclohexyl-2-nitroaniline

Product 1

HCID 19827791HCID 19827791, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

3.6 g (14.1 mmol) N-cyclohexyl-2-nitroaniline was dissolved in 50 ml ethanol and 150 ml ethylacetate. The solution was hydroqenated at atm. pressure by using Ra-Ni (1 g) as a catalyst. The reaction mixture was filtered and the filtrate was evaporated to give an oil. A mixture of the oil and 3.5 g (28 mmol) oxalic acid dihydrate in 100 ml 4N hydrochloric acid was refluxed for 2 h. After cooling to 25° C. the product was filtered off and washed with water to give 3.4 g (86%) 1-cyclohexyl-7-chlorquinoxaline-2,3(1H, 4H)-dione. M.p. (DSC) 310.6° C. 1H-NMR (DMSO-d6): 12.0 (1H, broad s), 7.7 (1H, s), 7.2 (2H, s), 4.2 (1H, broad, s) 2.0-1.0 (10H, m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customto give an oil
  4. temperaturewas refluxed for 2 h
  5. filtrationwas filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-b13921ac3c68461280f1e7bb32966ef0
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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