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

HRID 51318Notes

Reaction equation

HRID 51318 reaction equation
[C:1]1([CH2:7][N:8]2[C:20]3[CH2:19][CH:18]([CH3:21])[CH2:17][C:16](=[O:22])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:23]([O:25][CH3:26])=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[C:1]1([CH2:7][N:8]2[C:20]3[CH:19]=[C:18]([CH3:21])[CH:17]=[C:16]([OH:22])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:23]([O:25][CH3:26])=[O:24])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 227388359-[(phenyl)methyl]-5-carbomethoxy-2-methyl-1,2-dihydrocarbazol-4(3H)-one

Product 1

HCID 227397529-[(Phenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazoleYield 21%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the 9-[(phenyl)methyl]-5-carbomethoxy-2-methyl-1,2-dihydrocarbazol-4(3H)-one (1.30 g, 3.74 mM) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.93 g, 4.12 mM) in 37 mL of toluene was stirred between 80-90° C. for 5 hours. The mixture was purified by column chromatography on silica gel (elution with methylene chloride) to afford 270 mg (21%) of the 9-[(phenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole. 1H NMR (CDCl3) δ10.45 (s, 1H), 8.0 (d, J=8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.4 (dd, J=8 and 8 Hz, 1H), 7.3 (m, 3H), 7.05 (m, 2H), 6.65 (s, 1H), 6.6 (s, 1H), 5.5 (s, 2H), 4.1 (s, 3H), 2.45 (s, 3H). MS (ES) m/e 314, 346.

Workup

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

Sources & evidence

ORD record
ord-24108c552f6c4133890d196f7de326bc
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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