Hydrochloric Acid → (Z)-3-{4-Oxo-2-[(2-oxoindolin-3-ylidene)methyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}propanoic Acid

HRID 597848Notes

Reaction equation

HRID 597848 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][C:7]1[C:15]2[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=2[NH:9][C:8]=1/[CH:17]=[C:18]1\[C:19](=[O:27])[NH:20][C:21]2[C:26]\1=[CH:25][CH:24]=[CH:23][CH:22]=2)C.[OH-].[Na+].Cl>CCO>[C:4]([CH2:5][CH2:6][C:7]1[C:15]2[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=2[NH:9][C:8]=1/[CH:17]=[C:18]1\[C:19](=[O:27])[NH:20][C:21]2[C:26]\1=[CH:25][CH:24]=[CH:23][CH:22]=2)([OH:28])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 46847848(Z)-Ethyl 3-{4-Oxo-2-[(2-oxoindolin-3-ylidene)methyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}propanoate

Product 1

HCID 46846949(Z)-3-{4-Oxo-2-[(2-oxoindolin-3-ylidene)methyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}propanoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an EtOH solution (3.0 mL) containing (Z)-3-((3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1 H-indol-2-yl)methylene)indolin-2-one (0.50 mmol) was added 3.0 N aqueous NaOH (1.0 mL). The reaction was heated at reflux for 2.0 h and cooled to room temperature. The solution was acidified with 6 N HCl to pH 3.0. The resultant precipitate was filtered and washed with MeOH to provide the desired product. 1 H NMR (DMSO-d6) δ 13.76 (s, 1 H), 11.01 (s, 1 H), 7.77 (s, 1 H), 7.76 (d, 1 H), 7.17 (dd, 1 H), 7.01 (dd, 1 H), 6.89 (dd, 1 H), 3.15 (t, 2 H), 2.91 (t, 2H), 2.36-2.41 (m, 2 H), 2.06 (t, 2 H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2.0 h
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-be612bfc945f485883ab99c4aca91ea9
Source dataset
uspto-grants-2011_03
Patent number
US07897602B2

Reaction notes

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