2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 7-Nitroquinoline

HRID 494186Notes

Reaction equation

HRID 494186 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

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 2525137-Nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 119467-NitroquinolineYield 81.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe suspension was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give the crude product which
  5. customwas purified by flash column chromatography
  6. washElution with 30% EtOAc in 40-60° C. petroleum ether

Sources & evidence

ORD record
ord-fcf68eeae18247f48991d5cd281483db
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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