Acetic Acid → 2-(trifluoromethyl)quinoline-4-carboxylic acid

HRID 2286703Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[OH-].[K+].C(O)(=[O:16])C.C([O-])(=O)C.[Na+].[F:23][C:24]([F:29])([F:28])[C:25](=O)[CH3:26].Cl>O>[F:23][C:24]([F:29])([F:28])[C:25]1[CH:26]=[C:4]([C:2]([OH:16])=[O:3])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:1]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A 500 mL three-necked flask equipped with a stirrer, water condenser and thermometer was charged with fifteen grams (15 g) of isatin (0.10 mol), six grams (6 g) of potassium hydroxide (0.11 mol), and 100 mL of water. About 12 grams (12 g) of glacial acetic acid (0.20 mol) and 12 grams (12 g) of sodium acetate (0.14 mol) were then added to bring the pH of the mixture to 5±0.1. After the addition of 13.7 grams of trifluoroacetone (0.12 mol), the mixture was heated to 70° C. for 15 hours. At the end of this time, the mixture was acidified with 10% hydrochloric acid. A precipitate of 2-trifluoromethyl cinchoninic acid was obtained which was separated by filtration. The precipitate was washed with water until the wash water was clear, and then dried in air. About 18.8 grams of product was recovered, representing a yield of 76 percent.

Workup

customA 500 mL three-necked flask equipped with a stirrer, water condenser

Sources & evidence

ORD record: ord-a33f0ae5408a46798cca823cdce92bc4
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04267333

Reaction notes

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