Quinone → 1-(4-Diethylaminophenyl)-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester

HRID 420904Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[C:6]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][CH:15]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].[C:26]1(=O)[CH:31]=[CH:30][C:29](=[O:32])[CH:28]=[CH:27]1>CC#N>[CH2:1]([O:3][C:4]([C:5]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([OH:32])[CH:30]=2)[N:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH2:21][CH3:22])[CH2:23][CH3:24])=[CH:16][CH:15]=2)[C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:25])[CH3:2]

Participants

Conditions

Temperature: 4 °C

Procedure

A mixture of 3-(4-diethylaminophenylamino)pent-2-enedioic acid diethyl ester (11.9 g, 34.2 mmol, see step (a) above), 1,4-benzoquinone (4.62 g, 42.8 mmol) and anhydrous MeCN (70 mL) was stirred at 70° C. for 2 d and at 4° C. for 1 d. The solid was collected and recrystallized from MeCN. Yield 4.5 g (30%).

Workup

customThe solid was collected
customrecrystallized from MeCN

Sources & evidence

ORD record: ord-81546e2204864c7fa742fc6769b340bb
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097623B2

Reaction notes

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