4-(2-Hydroxyethyl)indolin-2-one → 3-[4-(3-dimethylamino-propyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one

HRID 2120243Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[CH3:14][N:15]([CH3:28])[CH2:16][CH2:17][CH2:18][C:19]1[C:20]([CH3:27])=[C:21]([CH:25]=O)[NH:22][C:23]=1[CH3:24]>N1CCCC1.C(O)C>[CH3:28][N:15]([CH3:14])[CH2:16][CH2:17][CH2:18][C:19]1[C:20]([CH3:27])=[C:21]([CH:25]=[C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[CH:12][C:4]=3[CH2:3][CH2:2][OH:1])[NH:8][C:7]2=[O:13])[NH:22][C:23]=1[CH3:24]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (177 mg, 1.0 mmol), 4-(3-dimethylamino-propyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (208 mg, 1.0 mmol) and 3 drops of pyrrolidine in 2.0 mL of ethanol was refluxed at 90° C. for 4 hours and cooled to room temperature. The precipitate was filtered, washed with cold ethanol and hexane, and dried in a vacuum oven overnight to give 360.6 mg (98%) of 3-[4-(3-dimethylamino-propyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one.

Workup

temperaturecooled to room temperature
filtrationThe precipitate was filtered
washwashed with cold ethanol and hexane
customdried in a vacuum oven overnight

Sources & evidence

ORD record: ord-deb07608bde0494ab8e5b5c6d779d6bd
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689806B1

Reaction notes

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