Nitric Acid → 4-Cyano-4'-(4-methoxycarbonylbutyrylamino)biphenyl

HRID 582156Notes

Reaction equation

HRID 582156 reaction equation
[H][H].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)#[N:4].[N+]([O-])(O)=O.C([N:23](C(C)C)C(C)C)C.[Cl-].[CH3:31][O:32][C:33](=[O:40])[CH2:34][CH2:35][CH2:36][C:37](O)=[O:38]>C(OCC)(=O)C.C(C1C=CC(C2C=CC([N+]([O-])=O)=CC=2)=CC=1)#N.C(Cl)Cl.[Pd]>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:23][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][C:33]([O:32][CH3:31])=[O:40])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)#[N:4]

Participants

10

Reactant 5

HCID 944Nitric AcidHCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 81531DiisopropylethylamineHCID 53445129Glutaric acid monomethylester chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 538293104-Cyano-4'-(4-methoxycarbonylbutyrylamino)biphenyl

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 52001084-Cyano-4'-nitrodiphenylSolvent2×

Procedure

Melting point: 171-173° C., prepared by reduction of 4-cyano-4'-nitro-biphenyl with hydrogen in the presence of palladium/charcoal in ethyl acetate, 4-cyano-4'-nitro-biphenyl is prepared by reacting 4-cyano-biphenyl with fuming nitric acid) and 5.8 g of N-ethyl-diisopropylamine are dissolved in 70 ml of methylene chloride and 5.6 g of glutaric acid monomethylester chloride are added with stirring. The mixture is stirred for two hours at ambient temperature. The organic phase is washed successively with 0.1N sodium hydroxide solution, 0.1N hydrochloric acid and water. After evaporation of the organic phase the residue is recrystallized from ethanol.

Workup

  1. customis prepared
  2. stirringThe mixture is stirred for two hours at ambient temperature
  3. washThe organic phase is washed successively with 0.1N sodium hydroxide solution, 0.1N hydrochloric acid and water
  4. customAfter evaporation of the organic phase the residue
  5. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-dc4d090c9ba544d7bf4bcc8ccc6b3bdc
Source dataset
uspto-grants-1999_07
Patent number
US05922763

Reaction notes

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