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

HRID 897134Notes

Reaction equation

HRID 897134 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) δ 1.82-1.87 (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-b94f517990114512bcf2d3604399b66c
Source dataset
uspto-grants-2005_07
Patent number
US06921767B2

Reaction notes

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