2-Pyridinecarboxaldehyde → HCID 54240908, compound

HRID 2120233Notes

Reaction equation

HRID 2120233 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.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=O>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:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1)[C:7](=[O:13])[NH:8]2

Participants

5

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 54240908HCID 54240908, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8082PiperidineSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (80 mg, 0.45 mmol) and 2-pyridinecarboxaldehyde (60 mg, 0.56 mmol) in 1% of piperidine in ethanol (5 mL) was heated at 90° C. for 8 hours. The reaction mixture was concentrated and the residue was chromatographed on a column of silica gel. It was then triturated with ethyl acetate and hexane to give 55 mg (46%) of 4-(2-hydroxy-ethyl)-3-pyridin-2-ylmethylene-1,3-dihydro-indol-2-one.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was chromatographed on a column of silica gel
  3. customIt was then triturated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-be72f0365ada474f9721b06a9a6135c8
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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