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

HRID 1713128Notes

Reaction equation

HRID 1713128 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>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

4

Reactant 1

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

Product 1

HCID 131938825,6,7,8-Tetrahydro-1,6-naphthyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6-Benzyl-5,6,7,8-tetrahydro-[1,6]naphthyridine (3.10 g, 13.82 mmol) is dissolved in acetic acid (40 ml). To the solution is added Pd—C (10%, 500 mg). The resulting mixture is hydrogenated under 40-50 psi at 55-60° C. for 10 hr. The solid catalyst is removed by filtration, and the filtering cake is washed with MeOH (20 ml×2). The combined organic phase is evaporated to dryness. The residue is taken up into water (25.0 ml), basified with saturated sodium carbonate solution, and extracted with EtOAc (30 ml×3). The combined organic phase is dried with sodium sulfate, and concentrated to give the title compound. MS (+VE) m/z 135.1 (M++1).

Workup

  1. customThe solid catalyst is removed by filtration
  2. washthe filtering cake is washed with MeOH (20 ml×2)
  3. customThe combined organic phase is evaporated to dryness
  4. extractionextracted with EtOAc (30 ml×3)
  5. dry with materialThe combined organic phase is dried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-108ffdb39f024c6b81a4bb88eec63a5f
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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