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

HRID 1815986Notes

Reaction equation

HRID 1815986 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>[Pd].CCO>[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 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-1,8-naphthyridine (18.5 g, 128 mmole), 10% Pd/C (5 g), and absolute EtOH (150 mL) was shaken under hydrogen (15 psi) on a Parr apparatus. After 24 hr, the mixture was filtered through celite®, and the filter pad was washed sequentially with absolute EtOH and EtOAc. The filtrate was concentrated to dryness to leave the title compound (18.85 g, 99%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.02 (d, J=7.5 Hz, 1H), 6.34 (d, J=7.5 Hz, 1 H), 4.80 (br s, 1 H), 3.38 (m, 2H), 2.74 (m, 2H), 2.30 (s, 3H), 1.88 (m, 2H); MS (ES) m/e 149 (M+H)+.

Workup

  1. filtrationthe mixture was filtered through celite®
  2. washthe filter pad was washed sequentially with absolute EtOH and EtOAc
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-8792934f87984be387c1350c644df6f3
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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