1-cyclohexyl-6-trifluoromethyl-7-nitro-2,3(1H,4H)-quinoxalinedione → 1-cyclohexyl-6-trifluoromethyl-7-amino-2,3(1H,4H)-quinoxalinedione

HRID 1458799Notes

Reaction equation

HRID 1458799 reaction equation
[CH:1]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([C:20]([F:23])([F:22])[F:21])=[C:14]([N+:17]([O-])=O)[CH:15]=3)[NH:10][C:9](=[O:24])[C:8]2=[O:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>O1CCCC1.[Pd]>[CH:1]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([C:20]([F:21])([F:22])[F:23])=[C:14]([NH2:17])[CH:15]=3)[NH:10][C:9](=[O:24])[C:8]2=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 220970691-cyclohexyl-6-trifluoromethyl-7-nitro-2,3(1H,4H)-quinoxalinedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 220971171-cyclohexyl-6-trifluoromethyl-7-amino-2,3(1H,4H)-quinoxalinedioneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

8 g (22.4 mmol) of 1-cyclohexyl-6-trifluoromethyl-7-nitro-2,3(1H,4H)-quinoxalinedione dissolved in 200 ml of tetrahydrofuran were hydrogenated under a pressure of about 1 bar of hydrogen in the presence of 1 g of palladium/active carbon (10% by weight Pd) at room temperature. The reaction mixture was filtered. Conventional workup of the filtrate gave a 100% yield of the abovementioned compound.

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-9917fb84cb264603b8b3f4a4d575800a
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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