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Oxindole → 2,4-Dimethyl-5-(2-oxo-1,2-Dihydro-Indol-3-Ylidenemethyl)-1H-Pyrrole-3-Carboxylic Acid (2-Diethylamino-Ethyl)Amide

HRID 1368498
Notes
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Reaction equation

HRID 1368498 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH2:11]([N:13]([CH2:28][CH3:29])[CH2:14][CH2:15][NH:16][C:17]([C:19]1[C:23]([CH3:24])=[C:22]([CH:25]=O)[NH:21][C:20]=1[CH3:27])=[O:18])[CH3:12]>N1CCCCC1.C(O)C>[CH2:28]([N:13]([CH2:11][CH3:12])[CH2:14][CH2:15][NH:16][C:17]([C:19]1[C:23]([CH3:24])=[C:22]([CH:25]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])[NH:21][C:20]=1[CH3:27])=[O:18])[CH3:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 321710OxindoleHCID 20761785N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Product 1

HCID 728166042,4-Dimethyl-5-(2-oxo-1,2-Dihydro-Indol-3-Ylidenemethyl)-1H-Pyrrole-3-Carboxylic Acid (2-Diethylamino-Ethyl)AmideYield 55.5%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalyst
HCID 702
Ethanol
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1,3-dihydro-indol-2-one (266 mg, 2 mmol), 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (530 mg, 2 mmol) and piperidine (1 drop) in ethanol was heated at 90° C. for 2 hours. The reaction was cooled to room temperature, the resulting precipitate was collected by vacuum filtration, washed with ethanol and dried to give 422 mg (55%) of the title compound as a light yellow solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe resulting precipitate was collected by vacuum filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-17bb23c285b2420ebf223d3a0d94b5ab
Source dataset
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06573293B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes