Thionyl Chloride → 8-{3-[Chloro-(4-chloro-phenyl)-methyl]-phenyl}-6-isopropyl-quinoline

HRID 896682Notes

Reaction equation

HRID 896682 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:26]([CH3:28])[CH3:27])[CH:19]=[C:20]4[C:25]=3[N:24]=[CH:23][CH:22]=[CH:21]4)[CH:11]=2)O)=[CH:4][CH:3]=1.O=S(Cl)[Cl:31]>C1C=CC=CC=1>[Cl:31][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[C:18]([CH:26]([CH3:28])[CH3:27])[CH:19]=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22350111(4-Chloro-phenyl)-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-methanol

Product 1

HCID 223501108-{3-[Chloro-(4-chloro-phenyl)-methyl]-phenyl}-6-isopropyl-quinoline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (4-chloro-phenyl)-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-methanol from Step 1 (1.0 g, 2.58 mmol) in benzene (7 mL) at 0° C. was added SOCl2 (0.375 mL, 5.2 mmol) dropwise. After 45 min. at 0-10° C., the resulting reaction mixture was filtered through silica gel and celite and then concentrated.

Workup

  1. customthe resulting reaction mixture
  2. filtrationwas filtered through silica gel and celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d447cc416d6a405e921c1340ad9667f7
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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