Hydrochloric Acid → 4'-ethyl-N-(4-methylphenyl)-[1,1'-biphenyl]-4-amine

HRID 52815Notes

Reaction equation

HRID 52815 reaction equation
C([N:4]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.C(O)C.Cl>C1(C)C=CC=CC=1>[CH2:17]([C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[CH:6][CH:7]=2)=[CH:16][CH:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 19375405N-acetyl-N-(4-methylphenyl)-4'-ethyl-[1,1'-biphenyl]-4-amine

Product 1

HCID 199639404'-ethyl-N-(4-methylphenyl)-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 19.96 g of the thus obtained N-acetyl-N-(4-methylphenyl) -4'-ethyl-[1,1'-biphenyl]-4-amine were added 150 ml of ethanol and 150 ml of concentrated hydrochloric acid. The reaction mixture was refluxed with stirring for 7 hours and then added to 1 l of ice water. The reaction mixture was then extracted with toluene and the obtained organic portion was washed with water two times, with a saturated aqueous solution of sodium hydrogencarbonate one time, and then with water two times, and dried by use of magnesium sulfate, and condensed under reduced pressure, whereby brown crystals were obtained. The thus obtained product was subjected to a silica gel column chromatography by use of toluene as an eluent, and recrystallized from a mixed solvent of n-hexane and toluene, whereby 4'-ethyl-N-(4-methylphenyl)-[1,1'-biphenyl]-4-amine (Aminobiphenyl Compound No. 2-62 in Table 3) was obtained in the form of colorless plates with a yield of 15.84 g (91.0%). The melting point of the product was 132.5° C. to 133.0° C.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. extractionThe reaction mixture was then extracted with toluene
  3. washthe obtained organic portion was washed with water two times, with a saturated aqueous solution of sodium hydrogencarbonate one time
  4. dry with materialwith water two times, and dried by use of magnesium sulfate, and condensed under reduced pressure, whereby brown crystals
  5. customwere obtained
  6. customrecrystallized from a mixed solvent of n-hexane and toluene

Sources & evidence

ORD record
ord-2eb34574e0374b6ba49016ef3cd6cf49
Source dataset
uspto-grants-1997_04
Patent number
US05616801

Reaction notes

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