Acetic Acid → 4-Chloro-6,7,8-trifluorocarbostyril

HRID 344889Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([F:14])[C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([O:15]CC)[CH:3]=1.Cl.C(O)(=O)C>O>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([F:14])[C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[NH:5][C:4](=[O:15])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 4-chloro-2-ethoxy-6,7,8-trifluoroquinoline (70.4 g) in 35% strength aqueous hydrochloric acid solution (170 cc), acetic acid (420 cc) and water (250 cc) is heated with stirring to a temperature in the region of 100° C. for 2 hours and a half. After cooling to approximately 20° C., the reaction mixture is poured into water (1100 cc) at approximately 5° C. and stirred for 15 minutes at this temperature and the insoluble matter is then drained and washed with water (3×220 cc). 4-Chloro-6,7,8-trifluorocarbostyril (61 g) is obtained in the form of a cream-colored solid, m.p. 213° C., which is used without further purification for the subsequent steps.

Workup

temperatureis heated
temperatureAfter cooling to approximately 20° C.
stirringstirred for 15 minutes at this temperature
washwashed with water (3×220 cc)

Sources & evidence

ORD record: ord-66509c66959c4f74a4944fea2424c698
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

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