Hydrochloric Acid → (3E)-3-{5,5-dimethyl-4-[4-(morpholin-4-ylmethyl)phenyl]furan-2(5H)-ylidene}-2-oxoindoline-5-carboxylic acid

HRID 2196149Notes

Reaction equation

[CH3:1][C:2]1([CH3:34])[O:6]/[C:5](=[C:7]2/[C:8](=[O:20])[NH:9][C:10]3[C:15]/2=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][CH:11]=3)/[CH:4]=[C:3]1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1([CH3:34])[O:6]/[C:5](=[C:7]2/[C:8](=[O:20])[NH:9][C:10]3[C:15]/2=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=3)/[CH:4]=[C:3]1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of methyl (3E)-3-{5,5-dimethyl-4-[4-(morpholin-4-ylmethyl)phenyl]furan-2(5H)-ylidene}-2-oxoindoline-5-carboxylate (18 mg, 0.039 mmol) in MeOH (1 mL) was added 1M NaOH solution (1 mL, 1 mmol). The mixture was heated in 50° C. bath under nitrogen for 4 hours, cooled to room temp, and neutralized with 1M HCl to about pH 7. The mixture was extracted with 10% MeOH/CHCl3 solution (3×30 mL). The organic layers were combined, dried over Na2SO4, and evaporated to dryness to give (3E)-3-{5,5-dimethyl-4-[4-(morpholin-4-ylmethyl)phenyl]furan-2(5H)-ylidene}-2-oxoindoline-5-carboxylic acid as yellow solid. Yield: 15 mg, 88%.

Workup

temperaturecooled to room temp
extractionThe mixture was extracted with 10% MeOH/CHCl3 solution (3×30 mL)
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-fd51fa28649743158a4749e8595ef5e6
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338415B2

Reaction notes

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