Delta-Valerolactone → HCID 33729537, compound

Temperature

135 °C

4,5-Dichlorobenzene-1,2-diamine (5.018 g, 28.4 mmol) was dissolved in HCl solution (4 M solution) (25 ml) at r.t. and delta-valerolactone (5.3 ml, 56.7 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) until the pH was 8. The mixture was extracted with EtOAc (3×100 ml) and the combined organic layers were dried over MgSO4, 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 as a purple solid (6.383 g, 87%): MS (ESI+) for C11H12Cl2N2O m/z 259.1 [M+H]+; LC purity 89% (ret. time, 1.23 min); 1H NMR (500 MHz, CDCl3) δ 7.56 (s, 2H), 3.55 (t, J=6.38 Hz, 2H), 2.86 (t, J=7.57 Hz, 2H), 1.84 (quin, J=7.68 Hz, 2H), 1.43-1.69 (m, 2H).

1. temperaturethen slowly cooled to r.t
2. customThe reaction was quenched by the addition of sat. NaHCO3 solution (200 ml) until the pH was 8
3. extractionThe mixture was extracted with EtOAc (3×100 ml)
4. dry with materialthe combined organic layers were dried over MgSO4
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-7cbea617f4944f76a435beef0bb946ae

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394310B2