1,8-Naphthyridine, 2-methyl- → 7-Methyl-1,2,3,4-tetrahydro-1,8-naphthyridine

HRID 497549Notes

Reaction equation

HRID 497549 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 740731,8-Naphthyridine, 2-methyl-

Product 1

HCID 223194667-Methyl-1,2,3,4-tetrahydro-1,8-naphthyridineYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The compound was prepared according to the procedure as described in WO 0033838. To a solution of 2-methyl-1,8-naphthyridine (2 g, 13.9 mmol) in ethanol (35 ml) was added 10% Pd/C, and the reaction mixture was stirred under H2 (10 psi) for 24 hours. Palladium was filtered out through celite and washed with excess ethanol. The filtrate was concentrated under vacuum to give 1.7 g (83%) pink solid. NMR (CD3OD) δ1.82-1.87 (m, 2H), 2.22 (s, 3H), 2.65-2.76 (m, 2H), 3.33-3.36 (m, 2H), 6.32 (d, 1H, J=7.25 Hz), 7.07 (d, 1H, J=7.38 Hz). Mass spectrometry: 149.15 (M+H)+.

Workup

  1. customThe compound was prepared
  2. filtrationPalladium was filtered out through celite
  3. washwashed with excess ethanol
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3d6f01e906954218ad08528f5fccf522
Source dataset
uspto-grants-2005_09
Patent number
US06949578B2

Reaction notes

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