Sulfuryl chloride → 2,5-Dichloro-4-methyl-6-(methyloxy)quinoline hydrochloride

HRID 1018025Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([Cl:13])[CH:7]=[C:6]2[CH3:14].S(Cl)([Cl:18])(=O)=O>C(O)(=O)C>[ClH:13].[Cl:13][C:8]1[CH:7]=[C:6]([CH3:14])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=2[Cl:18])[N:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A 10-liter, four-necked reactor equipped with a mechanical stirrer, condenser, thermowatch, addition funnel and a condenser was charged with 6-methoxy-4-methyl-2-chloroquinoline (3) (900 g, 4.33 moles) and glacial acetic acid (3.06 liters). The slurry was heated to 60° C. and a solution of sulfuryl chloride (646 g, 4.77 moles) in glacial acetic acid (0.902 liters) was added over 2 hours while maintaining the temperature between 60 and 65° C. The resulting slurry was stirred for 1 hour at 60-65° C., then cooled to 15-20° C. and stirred at this temperature for 2 hours. The product was removed by suction filtration, washed with cold (10° C.) acetic acid (0.550 liters), and air dried. to yield the title compound 978.4 g (81.2%); mp 159-160° C. (dec).

Workup

customA 10-liter, four-necked reactor equipped with a mechanical stirrer, condenser
additionthermowatch, addition funnel and a condenser
temperaturewhile maintaining the temperature between 60 and 65° C
temperaturecooled to 15-20° C.
stirringstirred at this temperature for 2 hours
customThe product was removed by suction filtration
washwashed with cold (10° C.) acetic acid (0.550 liters), and air
customdried

Sources & evidence

ORD record: ord-8dc51d81c95044e18a33e2271d1e3180
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479660B1

Reaction notes

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