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

HRID 234986Notes

Reaction equation

HRID 234986 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H][H].C(C1C=CC(C2C=CC=CC=2)=CC=1)#N.[N+]([O-])(O)=O.C(N(C(C)C)C(C)C)C.[Cl-].[CH3:46][O:47][C:48](=[O:55])[CH2:49][CH2:50][CH2:51][C:52](O)=[O:53]>C(OCC)(=O)C.C(C1C=CC(C2C=CC([N+]([O-])=O)=CC=2)=CC=1)#N.C(Cl)Cl.[Pd]>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:52](=[O:53])[CH2:51][CH2:50][CH2:49][C:48]([O:47][CH3:46])=[O:55])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

11

Reactant 6

HCID 944Nitric AcidHCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 81531DiisopropylethylamineHCID 971934-Amino-4'-cyanobiphenylHCID 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

6.6 g of 4-amino-4'-cyano-biphenyl (melting point: 171°-173° C., prepared by reduction of 4-cyano-4'-nitrobiphenyl with hydrogen in the presence of palladium/charcoal in ethyl acetate, 4-cyano-4'-nitrobiphenyl is prepared by reacting 4-cyano-biphenyl with fuming nitric acid) and 5.8 g of N-ethyldiisopropylamine 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-a7b31e64df53420e915866dc55de0803
Source dataset
uspto-grants-1997_01
Patent number
US05597825

Reaction notes

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