Delta-Valerolactone → HCID 178520563, compound

Temperature

135 °C

4-chloro-5-(trifluoromethyl)benzene-1,2-diamine (5.00 g, 23.74 mmol) was dissolved in HCl solution (4 M solution) (18.85 ml) at r.t. and delta-valerolactone (2.62 g, 26.12 mmol) was added slowly. The reaction was heated to 135° C. for 2 hrs then slowly cooled to r.t. The reaction was quenched by the addition of sat. NaHCO3 solution (200 ml) to pH 8. The mixture was extracted with EtOAc (3×150 ml) and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give the crude product as a brown solid which was triturated with ether (100 ml) to give the pure product (5.88 g, 84%): MS (ESI+) for C12H12ClF3N2O m/z 293.4 [M+H]+; LC purity 90% (ret. time, 1.49 min); 1H NMR (250 MHz, CHLOROFORM-d) δ ppm 1.39-1.72 (2H, m), 1.71-1.94 (2H, m), 2.87 (2H, t, J=7.61 Hz), 3.58 (2H, t, J=6.09 Hz), 7.42-7.96 (2H, m).

1. temperaturethen slowly cooled to r.t
2. customThe reaction was quenched by the addition of sat. NaHCO3 solution (200 ml) to pH 8
3. extractionThe mixture was extracted with EtOAc (3×150 ml)
4. dry with materialthe combined organic layers were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give the crude product as a brown solid which
8. customwas triturated with ether (100 ml)

ORD record

ord-5469857d3f8b4d71b6507ddac2ed49be

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394310B2