1,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(phenylmethyl)- → 5,6,7,8-Tetrahydro-1,6-naphthyridine

HRID 2247946Notes

Reaction equation

HRID 2247946 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[N:14]1[C:15]2[CH2:16][CH2:17][NH:8][CH2:9][C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 30587131,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(phenylmethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 131938825,6,7,8-Tetrahydro-1,6-naphthyridineYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine (5.0 g, 22.3 mmol) was dissolved in acetic acid (150 ml) and treated with 10% palladium on carbon (2.5 g). The reaction mixture was subjected to 40 psig hydrogen at 55° on a Parr hydrogenation apparatus for 18 hours; the mixture was then filtered through Super-Cel. The filtrate was evaporated to an amber oil, which was dissolved in 6N sodium hydroxide solution and extracted with toluene (2×50 ml) and methylene chloride (2×50 ml). The combined organic extracts were dried over magnesium sulfate, and concentrated in vacuo to provide the title product as a light amber oil (2.8 g, 21 mmol, 94% yield).

Workup

  1. filtrationthe mixture was then filtered through Super-Cel
  2. customThe filtrate was evaporated to an amber oil, which
  3. dissolutionwas dissolved in 6N sodium hydroxide solution
  4. extractionextracted with toluene (2×50 ml) and methylene chloride (2×50 ml)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f22145e006a4f8da3b7665b8b7b931c
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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