2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 7-Nitroquinoline
Reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (2.20 g, 12.3 mmol) in toluene (300 ml) was added 2,3-dichloro-5,6-dicyanobenzoquinone (5.88 g, 25.9 mmol) and the reaction was heated to 90° C. for 1.5 h. After cooling to room temperature, the suspension was filtered and the filtrate concentrated in vacuo to give the crude product which was purified by flash column chromatography. Elution with 30% EtOAc in 40-60° C. petroleum ether gave the title compound as a cream solid (1.74 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 9.08 (dd, 1H), 8.98 (d, 1H), 8.30 (dd, 2H), 7.99 (d, 1H), 7.62 (dd, 1H).