2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 9-[(Cyclopentyl)methyl]-4-hydroxy-5-carbomethoxy carbazole

HRID 51457Notes

Reaction equation

HRID 51457 reaction equation
[CH:1]1([CH2:6][N:7]2[C:19]3[CH2:18][CH2:17][CH2:16][C:15](=[O:20])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][C:12]=3[C:21]([O:23][CH3:24])=[O:22])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH:1]1([CH2:6][N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][C:12]=3[C:21]([O:23][CH3:24])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 227386049-[(cyclopentyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one

Product 1

HCID 227382539-[(Cyclopentyl)methyl]-4-hydroxy-5-carbomethoxy carbazoleYield 19.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 9-[(cyclopentyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (730 mg, 2.24 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (560 mg, 2.47 mmol) in 20 mL of toluene was heated at 80° C. for 3 hours. The mixture was purified directly by column chromatography on silica gel (elution with CH2Cl2) to afford 140 mg (0.433 mmol; 19%) of 9-[(cyclopentyl)methyl]-4-hydroxy-5-carbomethoxy carbazole as a yellow oil which slowly solidified. MS (ES) m/e 324 (M+1), 322 (M−1).

Workup

  1. customThe mixture was purified directly by column chromatography on silica gel (elution with CH2Cl2)

Sources & evidence

ORD record
ord-fdcd768c1b554915a04cab2f11b874e6
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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