Thionyl Chloride → 7-(Chlorophenylmethyl)quinoline

HRID 1756515Notes

Reaction equation

HRID 1756515 reaction equation
[C:1]1([CH:7]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:21])=O>ClCCl>[Cl:21][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19967113alpha-Phenyl-7-quinolinemethanol

Product 1

HCID 199671047-(Chlorophenylmethyl)quinolineYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.2 parts of intermediate 2, namely α-phenyl-7-quinolinemethanol, 8 parts of thionyl chloride and 65 parts of dichloromethane was stirred for 4 hours at room temperature. The reaction mixture was evaporated and the residue was poured into water. The product was extracted with dichloromethane (3×39 parts) and the combined extracts were dried, filtered and evaporated, yielding 3.4 parts (98.5%) of 7-(chlorophenylmethyl)quinoline (interm. 23).

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was poured into water
  3. extractionThe product was extracted with dichloromethane (3×39 parts)
  4. customthe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-725cce31484f40b49f7cbd10520a71ab
Source dataset
uspto-grants-1995_08
Patent number
US05441954

Reaction notes

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