3-Pyridinecarboxaldehyde → HCID 117940286, compound

HRID 62278Notes

Reaction equation

HRID 62278 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][O:16][CH2:15][CH2:14]1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=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:19]\[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)/[C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 1179401286-Methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 117940286HCID 117940286, compound

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 13 (0.1 g, 0.404 mmol) in MeOH/H2O (1:1) was added nicotinaldehyde 241 (0.052 g, 0.484 mmol) and NaOH (0.032 g, 0.808 mmol). The reaction was stirred at RT for 6 h, 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 242 was eluted at 30% ethyl acetate in hexane to afford yellow coloured solid (E)-6-methoxy-5-morpholino-2-(pyridin-3-ylmethylene)-2,3-dihydro-1H-inden-1-one 242.

Workup

  1. washwashed with water (3×25 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated
  4. customto get the crude, which
  5. customwas purified through flash chromatography
  6. washThe compound 242 was eluted at 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-52254e9e48e4418b87446d687f3fac69
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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