Thionyl Chloride → 7-(Chlorophenylmethyl)quinoline

HRID 2081601Notes

Reaction equation

HRID 2081601 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). In a similar manner there were also prepared the intermediates listed in Table 2.

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-147f3dbb59bd45159aa50559ed85e1fd
Source dataset
uspto-grants-1993_02
Patent number
US05185346

Reaction notes

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