Hydrochloric Acid → 3-[2-(6-methoxy-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid

HRID 1860941Notes

Reaction equation

[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:27])=[C:8](C(O)=O)[NH:9][C:10]=1[CH:11]=[C:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[NH:14][C:13]1=[O:23])([OH:3])=[O:2].[OH-].[K+].O.Cl>C(O)CO>[CH3:22][O:21][C:17]1[CH:16]=[C:15]2[C:20]([C:12](=[CH:11][C:10]3[NH:9][CH:8]=[C:7]([CH3:27])[C:6]=3[CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:13](=[O:23])[NH:14]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 200 °C

Procedure

4-(2-carboxyethyl)-3-methyl-5-(6-methoxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (501 mg) suspended in ethylene glycol (10 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 (2 pellets) was added. The mixture was then stirred at 90° C. for 30 minutes, after which time it was cooled, poured into water, and acidified with 2 N hydrochloric acid to pH 2. The precipitate was filtered, washed with water, and dried in a vacuum oven overnight to give 221 mg (48%) of 3-[2-(6-methoxy-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid.

Workup

temperatureThe reaction mixture was cooled to 90° C.
temperatureafter which time it was cooled
filtrationThe precipitate was filtered
washwashed with water
customdried in a vacuum oven overnight

Sources & evidence

ORD record: ord-7f948c13d430449b90493d3f4a905a15
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531502B1

Reaction notes

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