4-Butylaniline → HCID 2735693, compound

Temperature

0 °C

Sodium nitrite (11.74 g, 0.17 mol) in water (50 mL) was added over 30 min to an ice-cooled and stirred suspension of 4-n-butylaniline (24.30 g, 0.16 mol) in 6 N hydrochloric acid (190 mL). After an additional 15 min, a suspension of tin chloride dehydrate (108.3 g, 0.4 mol) in 6 N hydrochloric acid (190 mL) was added slowly, and the resulting suspension was stirred at 0° C. for 3 h. The solid was filtered and dissolved in a mixture of 40% potassium hydroxide solution (200 mL) and ethyl acetate (200 mL). The organic layer was separated and the aqueous layer was further extracted with ethyl acetate. The combined organic extracts were washed with 10% hydrochloric acid (120 mL), a solid started to develop in the organic layer. After cooled it to 0° C., the solid was filtered. The organic layer was separated, dried over Na2SO4, and the solvent was evaporated. The resulting solid was recrystallized from ethanol to afford a white solid (17.35 g, 54%). 1H NMR (300 MHz, DMSO-d6): δ 10.18 (s, 3H), 7.10 (d, 2H, J=8.4 Hz), 6.92 (d, 2H, J=8.7 Hz), 2.51 (t, 2H, J=7.5 Hz), 1.50 (pentet, 2H, J=7.5 Hz), 1.27 (sextet, 2H, J=7.8 Hz), 0.88 (t, 3H, J=7.5 Hz).

1. temperaturecooled
2. additionwas added slowly
3. stirringthe resulting suspension was stirred at 0° C. for 3 h
4. filtrationThe solid was filtered
5. dissolutiondissolved in a mixture of 40% potassium hydroxide solution (200 mL) and ethyl acetate (200 mL)
6. customThe organic layer was separated
7. extractionthe aqueous layer was further extracted with ethyl acetate
8. washThe combined organic extracts were washed with 10% hydrochloric acid (120 mL)
9. filtrationthe solid was filtered
10. customThe organic layer was separated
11. dry with materialdried over Na2SO4
12. customthe solvent was evaporated
13. customThe resulting solid was recrystallized from ethanol

ORD record

ord-5df328fe7cfa4ae9b7e0828bec02fd12

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343636B2