Methanol → 4-(2-Chlorophenyl)-7-ethyl-9-hydroxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

HRID 11156

Reaction equation

HRID 11156 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[C:12]=2[C:11]2[C:19]3[CH:25]=[C:24]([OH:26])[CH:23]=[C:22]([CH:27]=[CH2:28])[C:20]=3[O:21][C:10]=2[CH:9]=1.CO.[H][H]>[Ni].O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[C:12]=2[C:11]2[C:19]3[CH:25]=[C:24]([OH:26])[CH:23]=[C:22]([CH2:27][CH3:28])[C:20]=3[O:21][C:10]=2[CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 219807084-(2-Chlorophenyl)-9-hydroxy-7-vinyl-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 219806774-(2-Chlorophenyl)-7-ethyl-9-hydroxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dioneYield 59%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (863) (0.054 g, 0.167 mmol) prepared as described in example 444 in a methanol:tetrahydrofuran mixture (1:1, 4 mL) was hydrogenated over Raney nickel (100 mg) and hydrogen. The product was purified by column chromatography using a gradient of 0–100% ethyl acetate in dichloromethane to give (864) (0.032 g, 59%). 1H NMR δ [(CD3)2SO] 9.65 (s, 1H), 7.92 (m, 1H), 7.56 (d, J=3.0 Hz, 1H), 7.43 (m, 3H), 6.96 (d, J=2.5 Hz, 1H), 2.90 (q, 2H), 1.5 (t, 3H). MH−:392, 390.

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-62cae9a2d35848e7979fc9f2cc564996
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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