Hydrochloric Acid → 7-Chloro-6,8-difluoro-3-nitroquinoline

HRID 413041Notes

Reaction equation

[CH2:1]([N+:5]([O-:7])=[O:6])/[CH:2]=[N:3]\O.Cl.N[C:10]1[C:17]([F:18])=[C:16]([Cl:19])[C:15]([F:20])=[CH:14][C:11]=1[CH:12]=O>C(O)C>[Cl:19][C:16]1[C:17]([F:18])=[C:10]2[C:11]([CH:12]=[C:1]([N+:5]([O-:7])=[O:6])[CH:2]=[N:3]2)=[CH:14][C:15]=1[F:20]

Participants

Conditions

Temperature: 35 °C

Procedure

17.4 g of methazonic acid and 60 cm3 of a 37% aqueous hydrochloric acid solution were rapidly added, with stirring, to a solution of 8.7 g of 2-amino-4-chloro-3,5-difluorobenzaldehyde in 300 cm3 of ethanol, while the mixture was maintained at a temperature in the region of 35° C. The mixture was stirred for 16 hours at a temperature in the region of 20° C. The precipitate was dewatered and washed 3 times with 25 cm3 of diethyl ether. 8.1 g of 7-chloro-6,8-difluoro-3-nitroquinoline was obtained in the form of an orange-colored solid, which melted at 174° C.

Workup

washwashed 3 times with 25 cm3 of diethyl ether

Sources & evidence

ORD record: ord-2de4c20b14274734827d1d000d4e4b44
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566362B2

Reaction notes

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