Hydrochloric Acid → 3-[2-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid

HRID 24541Notes

Reaction equation

[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:26])=[C:8](C(O)=O)[NH:9][C:10]=1[CH:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:21])[NH:14][C:13]1=[O:22])([OH:3])=[O:2].[OH-].[K+].O.Cl>C(O)CO>[CH3:21][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[C:12](=[CH:11][C:10]1[NH:9][CH:8]=[C:7]([CH3:26])[C:6]=1[CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:13](=[O:22])[NH:14]2

Participants

Conditions

Temperature: 200 °C

Procedure

4-(2-carboxyethyl)-3-methyl-5-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (300 mg) suspended in ethylene glycol (5 mL) was heated in a sealed tube in a pre-heated oil bath at 200° C. for 2 hours. The reaction mixture was cooled to 90° C. and potassium hydroxide (1 pellet) was added. It was then stirred at 90° C. for 30 minutes. The reaction mixture was cooled, poured into water, and acidified with 2 N hydrochloric acid to pH 2. The precipitate was filtered, washed with water, and purified on a silica gel column to give 115 mg (44% yield) of 3-[2-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid.

Workup

temperatureThe reaction mixture was cooled to 90° C.
temperatureThe reaction mixture was cooled
filtrationThe precipitate was filtered
washwashed with water
custompurified on a silica gel column

Sources & evidence

ORD record: ord-72cd8fbe9b854a448083ef3a66a5476f
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855730B2

Reaction notes

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