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

HRID 1084397Notes

Reaction equation

HRID 1084397 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

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 542558274-Chloro-2-ethoxy-6,7,8-trifluoroquinoline

Product 1

HCID 537467124-Chloro-6,7,8-trifluorocarbostyrilYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A suspension of 70.4 g of 4-chloro-2-ethoxy-6,7,8-trifluoroquinoline in 170 cm3 of a 35% aqueous solution of hydrochloric acid, 420 cm3 of acetic acid and 250 cm3 of water is heated, with stirring, at a temperature close to 100° C. for 2 hours and a half. After cooling to about 20° C., the reaction mixture is poured into 1,100 cm3 of water at about 5° C., the mixture is stirred for 15 minutes at this temperature and the insoluble matter is then drained and washed with 3 times 220 cm3 of water. 61 g of 4-chloro-6,7,8-trifluorocarbostyril are obtained in the form of a cream solid melting at 213° C., which is used for the subsequent steps without further purification.

Workup

  1. temperatureis heated
  2. customclose to 100° C. for 2 hours
  3. stirringthe mixture is stirred for 15 minutes at this temperature
  4. washwashed with 3 times 220 cm3 of water

Sources & evidence

ORD record
ord-6175d871c6a84b89a1339c99824788c1
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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