3-Pyridinecarboxaldehyde → HCID 117940092, compound

HRID 62279Notes

Reaction equation

HRID 62279 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1.[OH-].[Na+]>CO.O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7]/[C:8](=[CH:20]\[C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)/[C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 117940223HCID 117940223, compound

Product 1

HCID 117940092HCID 117940092, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 6-methoxy-5-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-1-one 253 (0.1 g, 0.384 mmol) in MeOH/H2O (1:1) was added nicotinaldehyde (0.049 g, 0.461 mmol) and NaOH (0.03 g, 0.768 mmol) was added to the reaction mass, which was then stirred at RT for 6 h. The reaction mass was diluted with chloroform and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 30% ethyl acetate in hexane to afford yellow coloured solid (E)-6-methoxy-5-(4-methylpiperazin-1-yl)-2-(pyridin-3-ylmethylene)-2,3-dihydro-1H-inden-1-one 254.

Workup

  1. additionwas added to the reaction mass, which
  2. washwashed with water (3×25 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customto get the crude, which
  6. customwas purified through flash chromatography
  7. washThe compound was eluted at 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8795331195ad4e518fea554638949ae8
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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