Thionyl Chloride → 3-Chloromethyl-1-methyl-7-trifluoromethyl-4-quinolone hydrochloride

HRID 543675Notes

Reaction equation

HRID 543675 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([C:18]([F:21])([F:20])[F:19])=[CH:13][CH:14]=2)[N:9]([CH3:22])[CH:8]=1>ClCCl>[ClH:3].[Cl:3][CH2:6][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([C:18]([F:21])([F:20])[F:19])=[CH:13][CH:14]=2)[N:9]([CH3:22])[CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 128078823-Hydroxymethyl-1-methyl-7-trifluoromethyl-4-quinolone

Product 1

HCID 136693393-Chloromethyl-1-methyl-7-trifluoromethyl-4-quinolone hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of thionyl chloride (2.32 g.) in dichloromethane (100 ml.) was added during 1.5 hours to a refluxing suspension of finely ground 3-hydroxymethyl-1-methyl-7-trifluoromethyl-4-quinolone (5.0 g.) in dichloromethane (200 ml.). The solution was boiled under reflux for a further 0.5 hours then evaporated to dryness under reduced pressure to give the novel 3-chloromethyl-1-methyl-7-trifluoromethyl-4-quinolone hydrochloride, m.p. 182°-189°.

Workup

  1. temperatureunder reflux for a further 0.5 hours
  2. customthen evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f49e035348ec499f99432a68eea5733d
Source dataset
uspto-grants-1984_05
Patent number
US04447435

Reaction notes

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