2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21923197, compound

HRID 1020901Notes

Reaction equation

HRID 1020901 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[C:15]([CH:17]1[CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:28]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:19]2[CH2:35][CH2:36][CH2:37][C:18]1=2)#[N:16]>C1(C)C=CC=CC=1>[C:15]([C:17]1[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:28]2[C:20]([NH:21][C:22]3[C:27]2=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:19]2[CH2:35][CH2:36][CH2:37][C:18]=12)#[N:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21923192Ethyl 4-cyano-1,2,3,4,5,10-hexahydrocyclopenta[a]carbazole-5-carboxylate

Product 1

HCID 21923197HCID 21923197, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

DDQ (39 mg, 0.17 mmol, 220 mol %) was added to solution of ethyl 4-cyano-1,2,3,4,5,10-hexahydrocyclopenta[a]carbazole-5-carboxylate (24 mg, 0.078 mmol) in toluene (12 mL). The solution immediately turned dark brown, and was stirred at 20° C. for 1.5 hr. The solvent was evaporated. The residue was dissolved in EtOAc and rinsed with dilute aqueous ascorbic acid and twice with saturated NaHCO3. Evaporation of the solvent afforded crude product (21 mg) which was recrystallized from EtOAc gave the product (9 mg, 38% yield) as a beige solid, mp 229-231° C. NMR (CDCl3) δ 8.28 (s, 1H), 7.49 (s, 2H), 7.26 (s, 2H), 4.64 (q, 2H), 3.30 (t, 2H), 3.20 (t, 2H), 2.36 (quintet, 2H), 1.54 (t, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washrinsed with dilute aqueous ascorbic acid and twice with saturated NaHCO3
  4. customEvaporation of the solvent
  5. customafforded crude product (21 mg) which
  6. customwas recrystallized from EtOAc

Sources & evidence

ORD record
ord-5a8fd94c0fa6468e9bab20c4dc700949
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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