2-Chlorophenol → 8-Chloro-4-(2-chlorophenoxy)quinoline

HRID 2255429Notes

Reaction equation

HRID 2255429 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20]>C(OCC)(=O)C>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[Cl:13]

Participants

4

Reactant 2

HCID 72452-ChlorophenolHCID 889734,8-Dichloroquinoline2×

Product 1

HCID 1641768-Chloro-4-(2-chlorophenoxy)quinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2.0 g of 4,8-dichloroquinoline and 2.6 g of 2-chlorophenol was heated to 160° C. and stirred. Progress of the reaction was monitored by TLC. When no 4,8-dichloroquinoline remained, the reaction mixture was diluted with ethyl acetate, and washed with base to remove most of the excess phenol. To remove phenol remaining after washing, the product was purified using HPLC. Fractions containing product were combined, and solvent was removed using reduced pressure. The oily product crystallized. Yield: 1.36 g (46%). M.P. 56°-58° C.

Workup

  1. washwashed with base
  2. customto remove most of the excess phenol
  3. customTo remove phenol remaining
  4. washafter washing
  5. customthe product was purified
  6. additionFractions containing product
  7. customsolvent was removed
  8. customThe oily product crystallized

Sources & evidence

ORD record
ord-34f41e1e9ec14f71baae171abbcd6d20
Source dataset
uspto-grants-1993_08
Patent number
US05240940

Reaction notes

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