Hydrochloric Acid → 1-cyclohexyl--cyanoquinoxaline-2,3(1H,4H)-dione

HRID 1709218Notes

Reaction equation

[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11](C#N)=[CH:10][C:9]=2[N+:16]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:21]([CH2:24]C)CC)C.[CH2:26]([OH:28])[CH3:27].Cl.C(OCC)(=[O:32])C>[Pd]>[CH:1]1([N:7]2[C:8]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:16]([C:24]#[N:21])[C:26](=[O:28])[C:27]2=[O:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1.2 g (4.9 mmol N-Cyclohexyl-4-cyano-2-nitroaniline 100 ml ethyl acetate was hydrogenated at 40 psi by using 5% Pd/C (100 mg) as a catalyst. The reaction mixture was filtered and 2.0 g (20 mmol) dry triethylamine was added. A solution of 2.7 g (20 mmol) ethyl oxalyl chloride in 20 ml ethyl acetate was added dropwise and the reaction mixture was stirred for 3 h. The reaction mixture was filtered and evaporated in vacuo to give an oil. A mixture of the oil, 20 ml ethanol and 70 ml 0.5 N hydrochloric acid was refluxed for 1 h. After cooling to 25° C. the precipitate was filtered off and washed with water to give 0.33 g (25 %) 1-cyclohexyl--cyanoquinoxaline-2,3(1H,4H)-dione. M.p.(DSC): decomp. 1H-NMR (DMSO-d6): 12.0 )1H, broad s), 8.0-7.4 (3H, m), 4.4 (1H, m), 2.7-0.7 (10H, m). IR (KBr): 2450, 1700 cm -1.

Workup

filtrationThe reaction mixture was filtered
filtrationThe reaction mixture was filtered
customevaporated in vacuo
customto give an oil
temperaturewas refluxed for 1 h
filtrationwas filtered off
washwashed with water

Sources & evidence

ORD record: ord-27f6e0ec4d7d4674b630274f9b814c7f
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948794

Reaction notes

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