7-Bromo-2-(3-pyridylmethylene)-1-tetralone → 7-Bromo-2-(3-pyridylmethyl)-1-tetralone

HRID 280621Notes

Reaction equation

HRID 280621 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[CH:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 539223587-Bromo-2-(3-pyridylmethylene)-1-tetraloneHCID 178418361HCID 178418361, compound

Product 1

HCID 233208987-Bromo-2-(3-pyridylmethyl)-1-tetraloneYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7-bromo-2-(3-pyridylmethylene)-1-tetralone (13.9 g) in ethanol (150 ml) containing 5% palladium on charcoal (0.50 g) was hydrogenated at 25° and 4 atm. pressure until the theoretical quantity of hydrogen had been taken up. The catalyst was filtered off and the filtrate was evaporated. The residue was distilled to give an oil (12.0 g), b.p. 200°-240° at 1.0 mm containing ca 40% of debrominated material. The product was purified by high pressure liquid chromatography using a silica gel column and a mixture of hexane and ethyl acetate (45:55) as eluent. Debrominated product was eluted first followed by pure 7-bromo-2-(3-pyridylmethyl)-1-tetralone, m.p. 63°-67°.

Workup

  1. customwas hydrogenated at 25°
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-c0565fa361a14ef2af64f216c89619b6
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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