Cyclohexene → 3-Amino-N-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamide

HRID 637489Notes

Reaction equation

HRID 637489 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[CH:18][C:19](=[O:22])[NH:20][CH:21]=2)=[CH:12][CH:11]=1)=[O:8])([O-])=O.C1CCCCC=1>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[CH:18][C:19](=[O:22])[NH:20][CH:21]=2)=[CH:12][CH:11]=1)=[O:8]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 138535683-Nitro-N-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamide

Product 1

HCID 138535693-Amino-N-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamideYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-[4-(3-Nitrobenzamido)phenyl]-2(1H)-pyrazinone was reduced with cyclohexene and palladium on charcoal in ethanol in a manner similar to that described in Example 6 to give the title compound (60%) m.p.>250° C.; δ(DMSO-d6) 8.01 and 8.10 (2H, ABq, pyrazinone ring protons), ##STR15## ν(Nujol mull) 1525 (--NHCO), 1660 (C=0) cm-1.

Sources & evidence

ORD record
ord-1b628cbc7822400bac117dec9f3757a3
Source dataset
uspto-grants-1985_12
Patent number
US04556711

Reaction notes

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