2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58093392, compound

Temperature

0 °C

A solution 7-bromo-2,3,4,9-tetrahydro-1H-carbazole (2.87 g, 11.5 mmol) in THF (103 mL) and H2O (11.5 mL) was cooled to 0° C. and treated with a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5.23 g, 23.1 mmol) in THF (46 mL) at such a rate that the reaction mixture did not exceed 4° C. The resulting solution was allowed to stir for an additional 45 min at 0° C. The solution was concentrated to dryness under reduced pressure. The resulting solids were suspended in EtOAc (100 mL) and saturated NaHCO3 solution (300 mL). The solids were collected by filtration and washed with additional saturated NaHCO3 solution (400 mL) followed by H2O (150 mL). The solid was dried to provide the title compound (2.46 g, 81%) as a light pink solid: 1H NMR (500 MHz, DMSO-d6) δ 11.97 (s, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.58 (d, J=1.5 Hz, 1H), 7.27 (dd, J=8.5, 2.0 Hz, 1H), 2.95 (t, J=6.0 Hz, 2H), 2.42 (t, J=6.0 Hz, 2H), 2.14-2.09 (m, 2H); ESI MS m/z 263 [M+H]+.

1. customdid not exceed 4° C
2. concentrationThe solution was concentrated to dryness under reduced pressure
3. filtrationThe solids were collected by filtration
4. washwashed with additional saturated NaHCO3 solution (400 mL)
5. customThe solid was dried

ORD record

ord-dd8212f1587840a29816c524b70b928f

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637501B2