HCID 54461484, compound → HCID 86752754, compound

HRID 963367Notes

Reaction equation

HRID 963367 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=O)[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:4]2[O:19][CH2:20][CH2:21][O:22][C:3]=12>C1COCC1.[Pd]>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:4]2[O:19][CH2:20][CH2:21][O:22][C:3]=12

Participants

4

Reactant 1

HCID 54461484HCID 54461484, compound

Product 1

HCID 86752754HCID 86752754, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-amino-5-chloro-2,3-ethylenedioxyphenyl)-3-(pyridin-4-yl)-2-propen-1-one (1.55 g, 5 mmol) in 50 mL of THF was hydrogenated over 5% palladium on carbon (0.5 g) for approximately 2 hours. The mixture was filtered and concentrated by rotary evaporation. Purification of the residue by silica gel chromatography (2% CH3OH--CH2 +0.1% NH4OH) gave 1-(4-amino-5-chloro-2,3-ethylenedioxyphenyl)-3-(pyridin-4-yl)propan.-1-one (1.23 g, 3.8 mmol)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated by rotary evaporation
  3. customPurification of the residue by silica gel chromatography (2% CH3OH--CH2 +0.1% NH4OH)

Sources & evidence

ORD record
ord-1faa0df5a9544ee8b77d48e1bb902351
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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