Hydrochloric Acid → 3-[2-(2-Oxo-1,2-dihydroindol-3-ylidenemethyl)-phenyl]-propionic acid

HRID 1860933Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To 300 mg of ethyl (E)-3-[(2-oxo-1,2-dihydroindol-3-ylidenemethyl)phenyl]-propionate in 3 mL of ethanol was added 2 mL of 2N sodium hydroxide. The mixture was stirred at 90° C. for 2 hrs, cooled and acidified with 6 N hydrochloric acid to pH 3. The solid was collected by filtration and washed with cold ethanol to give 30 mg of 3-[2-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-phenyl]-propionic acid as a yellow solid.

Workup

temperaturecooled
filtrationThe solid was collected by filtration
washwashed with cold ethanol

Sources & evidence

ORD record: ord-4bae5eff9ecc4d3c843258848e620af5
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531502B1

Reaction notes

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