Sodium Hydroxide → 3-{2,4-Dimethyl-5-[(2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid

HRID 1937544Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

Alternatively, a mixture of 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid (10 g, 51 mmol), 2-oxindole (6.5 g, 49 mmol) and sodium hydroxide (40 g, 58 mmol) dissolved in 50 ml of water was stirred at 50° C. for 4 hours. The reaction mixture was cooled to room temperature, filtered and the filtrate acidified with to pH 3 with 12 N hydrochloric acid. The solid which precipitated was collected by vacuum filtration, washed with 10 ml of water and dried under vacuum overnight. The crude solid slurry washed with hot ethanol twice. The solid was then collected by vacuum filtration, washed with 10 ml of ethanol and dried under vacuum to give 13.8 g (91%) of 3-[2,4-dimethyl-5-(2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrol-3-yl]-propionic acid.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
customThe solid which precipitated
filtrationwas collected by vacuum filtration
washwashed with 10 ml of water
customdried under vacuum overnight
washThe crude solid slurry washed with hot ethanol twice
filtrationThe solid was then collected by vacuum filtration
washwashed with 10 ml of ethanol
customdried under vacuum

Sources & evidence

ORD record: ord-82f7ed97dcb94ff3baf7fe715a4be002
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06395734B1

Reaction notes

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