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

HRID 51358Notes

Reaction equation

HRID 51358 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:21]3[CH2:20][CH2:19][CH2:18][C:17](=[O:22])[C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[C:23]([O:25][CH3:26])=[O:24])[CH:5]=[CH:6][CH:7]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:22])[C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[C:23]([O:25][CH3:26])=[O:24])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 227386219-[(3-fluorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one

Product 1

HCID 227382959-[(3-Fluorophenyl)methyl]-4-hydroxy-5-carbomethoxy carbazoleYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the 9-[(3-fluorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (434.0 mg, 1.23 mM) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (324.0 mg, 1.42 mM) in 20 mL of toluene was stirred between 70-80° C. for 5 h. The mixture was purified directly by column chromatography on silica gel (elution with methylene chloride) to afford 137.0 mg (32%) of the 9-[(3-fluorophenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole as a yellow foam. 1H NMR (DMSO-d6) δ10.2 (s, 1H), 7.7 (d, 1H, J=8 Hz), 7.4 (t, 1H, J=8 Hz), 7.3 (m, 2H), 7.2 (d, 1H, J=8 Hz), 7.1 (d, 1H, J=8 Hz), 7.05-6.85 (m, 3H), 6.6 (d, 1H, J=8 Hz), 5.65 (s, 2H), and 3.85 (s, 3H). IR (CHCl3, cm−1) 3200 (br), 1687, 1597, 1452, 1442, 1285, and 1267. MS (ES) m/e 348, 350.

Workup

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

Sources & evidence

ORD record
ord-740e87da8b434d78b6fdff339e002e24
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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