4-Chloro-6,7,8-trifluorocarbostyril → 6,7,8-Trifluorocarbostyril

HRID 344888Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

4-Chloro-6,7,8-trifluorocarbostyril (60.83 g), suspended in acetic acid (520 cc) and triethylamine (38.15 cc), is hydrogenated under a pressure of 1 atmosphere at a temperature in the region of 25° C. in the presence of palladium on charcoal (5.25 g; 10% Pd) until the absorption of hydrogen is complete. The reaction mixture is then heated to approximately 40° C. and filtered at the same temperature through diatomaceous silica for filtration. The filtrate is concentrated under reduced pressure (20 kPa) at a temperature in the region of 50° C. The dry extract is taken up with water (400 cc); the insoluble matter is drained and washed with water (4×170 cc), ethanol (2×110 cc) and isopropyl ether (2×100 cc). 6,7,8-Trifluorocarbostyril (48.35 g) is obtained in the form of a colorless solid, subliming at 288° C., which is used without further purification for the subsequent steps.

Workup

customtriethylamine (38.15 cc), is hydrogenated under a pressure of 1 atmosphere at a temperature in the region of 25° C. in the presence of palladium on charcoal (5.25 g; 10% Pd) until the absorption of hydrogen
filtrationfiltered at the same temperature through diatomaceous silica for filtration
concentrationThe filtrate is concentrated under reduced pressure (20 kPa) at a temperature in the region of 50° C
extractionThe dry extract
washwashed with water (4×170 cc), ethanol (2×110 cc) and isopropyl ether (2×100 cc)

Sources & evidence

ORD record: ord-dc6373476152471a87c3a973dd422af5
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

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