3-(Trifluoromethyl)aniline → HCID 178468329, compound

Temperature

0 °C

3-(Trifluoromethyl)aniline (34.6 g, 215 mmol) was dissolved in a mixture of concentrated hydrochloric acid (64 mL) and water (64 mL). To the resulting mixture was added dropwise at 0° C. a solution of sodium nitrite (16.6 g, 240 mmol) in water (100 mL). The mixture was stirred for 1 h at 0° C. To the resulting diazonium salt solution was added dropwise a solution of pentane-2,4-dione (22.0 g, 220 mmol) and sodium acetate (52.5 g, 640 mmol) in ethanol (225 mL) and water (80 mL) at room temperature. The mixture was stirred for 18 h at room temperature with a mechanical stirrer. The orange precipitate was filtered off and washed with water (150 mL×3), 50 percent aqueous ethanol (100 mL×2), and n-hexane (100 mL), and then dried in vacuo at 50° C. for 5 h affording 52.7 g (90%) of 3-{[3-(trifluoromethyl)phenyl]hydrazono}pentane-2,4-dione as an orange solid.

1. stirringThe mixture was stirred for 18 h at room temperature with a mechanical stirrer
2. filtrationThe orange precipitate was filtered off
3. washwashed with water (150 mL×3), 50 percent aqueous ethanol (100 mL×2), and n-hexane (100 mL)
4. customdried in vacuo at 50° C. for 5 h

ORD record

ord-ff5d870c1be14b78ae9e340d89177ad4

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916566B2