Thionyl Chloride → HCID 86675782, compound

HRID 69074Notes

Reaction equation

HRID 69074 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12]O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[CH:8]=2)[N:3]=1.S(Cl)([Cl:23])=O>C(Cl)Cl>[Cl:1][C:2]1[C:11]([CH2:12][Cl:23])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86675781(2-Chloro-6-o-tolylquinolin-3-yl)methanol

Product 1

HCID 86675782HCID 86675782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (6-bromo-2-chloroquinolin-3-yl)methanol (19.8 g, 72.5 mmol, prepared as in example 2, step 2), o-tolylboronic acid (10.4 g, 76.1 mmol), potassium acetate (21.3 g, 217.4 mmol) and dichlorobis(4-(di-tert-butylphosphino)-N,N-dimethylaniline)palladium (II) (0.51 g, 0.72 mmol) in CH3CN (300 ml) and water (100 ml) was heated in to reflux. After 2 h, the reaction was allowed to cool to RT and the aqueous phase was discarded. The organics were washed with 2×50% brine/water, and then 2× brine. The organics were concentrated to ˜100 mL, at which point the precipitate was filtered off to afford a pale yellow solid of (2-chloro-6-o-tolylquinolin-3-yl)methanol. Step 2: (2-chloro-6-o-tolylquinolin-3-yl)methanol (13.9 g, 49.0 mmol) was treated with DCM (100 ml) and thionyl chloride (106 ml, 1456 mmol) at ambient temperature. After 15 min, the solution was concentrated and azeotroped with 2×100 mL toluene, to afford a yellow solid of 2-chloro-3-(chloromethyl)-6-o-tolylquinoline.

Workup

  1. concentrationthe solution was concentrated
  2. customazeotroped with 2×100 mL toluene

Sources & evidence

ORD record
ord-f9988b0b2c384f10b4f9c492215fa11c
Source dataset
uspto-grants-2014_09
Patent number
US08822485B2

Reaction notes

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