Indole-5-carboxaldehyde → 4-(2-hydroxy-ethyl)-3-(1H-indol-5-ylmethylene)-1,3-dihydro-indol-2-one

HRID 2120237Notes

Reaction equation

HRID 2120237 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[NH:14]1[C:22]2[C:17](=[CH:18][C:19]([CH:23]=O)=[CH:20][CH:21]=2)[CH:16]=[CH:15]1>N1CCCCC1.C(O)C>[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[CH:23][C:19]1[CH:18]=[C:17]3[C:22](=[CH:21][CH:20]=1)[NH:14][CH:15]=[CH:16]3)[C:7](=[O:13])[NH:8]2

Participants

5

Reactant 2

HCID 589040Indole-5-carboxaldehydeHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 539026074-(2-hydroxy-ethyl)-3-(1H-indol-5-ylmethylene)-1,3-dihydro-indol-2-oneYield 72%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (39 mg, 0.22 mmol), 1H-indole-5-carbaldehyde (32 mg, 0.22 mmol) and 1 drop of piperidine in ethanol was heated at 90° C. for overnight and cooled to room temperature. The reaction mixture was concentrated and the residue was purified on silica gel column to give 48 mg (72%) of 4-(2-hydroxy-ethyl)-3-(1H-indol-5-ylmethylene)-1,3-dihydro-indol-2-one as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified on silica gel column

Sources & evidence

ORD record
ord-1ac0011f53ee44f88004f1ed02f52447
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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