2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21923227, compound

HRID 1020897Notes

Reaction equation

HRID 1020897 reaction equation
[C:1]([C:3]1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[C:15]([CH:17]1[C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=2[C:20]2[CH2:30][CH2:31][CH2:32][C:19]=2[CH:18]1[C:33]([O-:35])=[O:34])#[N:16]>C1(C)C=CC=CC=1>[C:15]([C:17]1[C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=2[C:20]2[CH2:30][CH2:31][CH2:32][C:19]=2[C:18]=1[C:33]([O:35][CH2:1][CH3:3])=[O:34])#[N:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21923233HCID 21923233, compound

Product 1

HCID 21923227HCID 21923227, compoundYield 252%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

DDQ (1.35 g, 5.95 mmol) was added to solution of 5-cyano-1,2,3,4,5,10-hexahydrocyclopenta[a]carbazole-4-carboxylate (820 mg, 2.66 mmol) in toluene (12 mL). The solution immediately turned dark brown, and was stirred at 60° C. for 3 hr. The mixture was cooled to 20° C. overnight and filtered. The precipitate was rinsed twice with hexanes to give 2.04 g of a light green solid. This was suspended in methanol (8 mL), filtered, and the precipitate rinsed with methanol (3 mL, in portions), and ether to give 603 mg (75% yield) of product as a light green solid, mp 233-234° C. NMR (CDCl3) δ 8.80 (d, 1H), 8.20 (s, 1H), 7.52 (m, 2H), 7.38 (t, 1H), 4.52 (q, 2H), 3.42 (t, 2H), 3.19 (t, 2H), 2.31 (quintet, 2H), 1.51 (t, 3H). Anal. Calcd for C19H16N2O2-0.2H2O: C, 74.11; H, 5.37; N, 9.10. Found: C, 74.03; H, 5.06; N, 9.04.

Workup

  1. temperatureThe mixture was cooled to 20° C. overnight
  2. filtrationfiltered
  3. washThe precipitate was rinsed twice with hexanes

Sources & evidence

ORD record
ord-7a99d1156c80491d864590e7f00ecba8
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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