4'-Fluoroacetophenone → 2,4-Bis(4-fluorophenyl)quinoline

HRID 1149

Reaction equation

HRID 1149 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=O.[CH3:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=O.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>O>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]2[CH:17]=[C:4]([C:6]3[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=3)[C:3]3[C:2](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:1]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 98372872-Amino-4'-fluorobenzophenoneHCID 124969952-Methylbenzenesulfonic acid hydrate

Product 1

HCID 196948162,4-Bis(4-fluorophenyl)quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A flask is loaded with (17) (21.5 g, 0.1 mol), 4-fluoroacetophenone (13.8 g, 0.1 mol), and toluene sulfonic acid monohydrate (3.8 g, 0.02 mol). The flask is heated to 200° C. and the water of condensation removed. After water evolution ceased, the mixture is cooled and the crude solid product is crushed and washed with hot ethanol The product is further recrystallized from toluene.

Workup

  1. customremoved
  2. temperaturethe mixture is cooled
  3. customthe crude solid product is crushed
  4. washwashed with hot ethanol The product
  5. customis further recrystallized from toluene

Sources & evidence

ORD record
ord-505bc94ed0b24d42b247b9173702273a
Source dataset
uspto-grants-1998_03
Patent number
US05723573

Linked notes

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