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Water → 3-[3-(4-methyl-1-phenyl-pent-(Z)-ylidene)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-benzoic acid

HRID 1623475
Notes
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Reaction equation

HRID 1623475 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)/[C:13](=[C:20](/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)\[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])/[C:12]2=[O:32])[CH:5]=1.O.O[Li].O>C1COCC1>[CH3:24][CH:23]([CH3:25])[CH2:22][CH2:21]/[C:20](=[C:13]1/[C:12](=[O:32])[N:11]([CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:33])=[O:2])[C:19]2[C:14]/1=[CH:15][CH:16]=[CH:17][CH:18]=2)/[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 510344403-{3-[4-methyl-1-phenyl-pent-(Z)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

Product 1

HCID 510345533-[3-(4-methyl-1-phenyl-pent-(Z)-ylidene)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-benzoic acidYield 47%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

3-{3-[4-Methyl-1-phenyl-pent-(Z)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (24 mg, 0.05 mmol) was dissolved in THF (1 ml) and water (1 ml) and LiOH.H2O (14 mg, 0.33 mmol) was added in one portion. The mixture was stirred at 50° C. for 16 h. The mixture was concentrated under reduced pressure and acidified to pH=3. Purification by preparative HPLC afforded 3-[3-(4-methyl-1-phenyl-pent-(Z)-ylidene)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-benzoic acid 10 mg. 1H NMR (300 Hz, CDCl3): δ ppm 0.88 (d, 6H), 1.36-1.44 (m, 2H), 1.64-1.68 (m, 1H), 3.33-3.38 (m, 2H), 5.04 (s, 2H), 6.01 (d, 1H), 6.58-6.61 (m, 2H), 6.96-7.02 (t, 1H), 7.26-7.29 (m, 2H), 7.37 (t, 2H), 7.43-7.52 (m, 3H), 7.93 (d, 1H), 8.03 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-3e40d30def2b47b298ddbaac0a287a39
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778973B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes