3-Methoxy-2,7-naphthyridine → 6-Methoxy-1,2,3,4-tetrahydro-2,7-naphthyridine

HRID 643493Notes

Reaction equation

HRID 643493 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[N:8][CH:7]=2>CC(O)=O.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][N:4]=1)[CH2:7][NH:8][CH2:9][CH2:10]2

Participants

4

Reactant 1

HCID 591643983-Methoxy-2,7-naphthyridine

Product 1

HCID 591643946-Methoxy-1,2,3,4-tetrahydro-2,7-naphthyridine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Crude 3-methoxy-2,7-naphthyridine (prepared from 4.4 mmol of 6-methoxy-4-[(trimethylsilyl)ethynyl]nicotinaldehyde) was hydrogenated (30 psi pressure) at RT over PtO2 (approx. 0.1 g) in HOAc (25 mL) for 2.5 h. The solution was filtered through a Celite pad and the clear filtrate was concentrated by freeze-drying to give crude 6-methoxy-1,2,3,4-tetrahydro-2,7-naphthyridine as the acetate salt.

Workup

  1. customat RT
  2. customfor 2.5 h
  3. filtrationThe solution was filtered through a Celite pad
  4. concentrationthe clear filtrate was concentrated
  5. customby freeze-drying

Sources & evidence

ORD record
ord-12652df9eabe4af0829eb15bf312f531
Source dataset
uspto-grants-2010_04
Patent number
US07700604B2

Reaction notes

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