4-Butylaniline → HCID 4763823, compound

Temperature

100 °C

To a flask equipped with a magnetic stirrer, reflux condenser, and a nitrogen inlet was added 4-n-butylaniline (48.5 grams, 0.325 moles), 1-fluoro-4-nitrobenzene (15.3 grams, 0.108 moles) and anhydrous methyl sulfoxide (120 ml). The contents of the flask were heated at 100° C. for 3 days; cooled to room temperature; partitioned between diethyl ether (300 ml) and water (100 ml). The ether extract was washed with water (4×100 ml) followed by brine (2×50 ml). The ether extract was dried over anhydrous magnesium sulfate, filtered and concentrated m vacuo to yield a brown oily residue. The residue was re-crystallized from hexane (300 ml) to yield 18.4 grams of product as a yellow solid. 1H NMR (CDCl3) δ 8.1(d, 2H), 7.2(d, 2H), 7.15(d, 2H), 6.9(d, 2H), 6.3(bs, 1H), 2.6(t 2H), 1.6(pent, 2H), 1.4(hextet, 2H), 0.9(t, 3H).

1. customTo a flask equipped with a magnetic stirrer
2. temperaturereflux condenser, and a nitrogen inlet
3. temperaturecooled to room temperature
4. custompartitioned between diethyl ether (300 ml) and water (100 ml)
5. extractionThe ether extract
6. washwas washed with water (4×100 ml)
7. extractionThe ether extract
8. dry with materialwas dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated m vacuo
11. customto yield a brown oily residue
12. customThe residue was re-crystallized from hexane (300 ml)

ORD record

ord-39e1e7bf405641069072ab7eb7479781

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683017B2