反应详情

温度

108 °C

4-Chloro-5-methyl-benzene-1,2-diamine (5.06 g; 32.3 mmoles) and 3,3,3-trifluoro-2-hydroxy-propionic acid (7.11 g; 49.4 mmoles) were suspended in 6N HCl (12 mL; 72 mmoles) under a nitrogen atmosphere. The reaction was stirred vigorously and heated to 108° C. for 18 hrs, then cooled to room temperature. The reaction was diluted with water (100 mL) and with ethyl acetate (100 mL), then sodium bicarbonate (9.12 g; 109 mmoles) was added slowly and in portions to quench the reaction. The aqueous layer was separated and extracted with ethyl acetate (3×40 mL). The extracts were combined, washed with water (30 mL) and brine (30 mL), then dried over Na2SO4. The filtrate was concentrated in vacuo to yield a crude brown solid which was then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2) to yield the title compound as a purple/brown solid.

1. temperaturecooled to room temperature
2. customto quench
3. customthe reaction
4. customThe aqueous layer was separated
5. extractionextracted with ethyl acetate (3×40 mL)
6. washwashed with water (30 mL) and brine (30 mL)
7. dry with materialdried over Na2SO4
8. concentrationThe filtrate was concentrated in vacuo
9. customto yield a crude brown solid which
10. customwas then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2)