Potassium Acetate → 1,2,3,4-Tetrahydro-2,7-naphthyridine

HRID 712486Notes

Reaction equation

HRID 712486 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8](Cl)=[N:9][C:10]=2Cl)[CH:5]=[C:4](Cl)[N:3]=1.C([O-])(=O)C.[K+]>CO.[Pd]>[CH2:10]1[C:11]2[C:6](=[CH:5][CH:4]=[N:3][CH:2]=2)[CH2:7][CH2:8][NH:9]1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 5178723HCID 5178723, compound

Product 1

HCID 178014131,2,3,4-Tetrahydro-2,7-naphthyridineYield 125.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,3,6,8-tetrachloro-2,7-naphthyridine (1.00 g, 2.67 mmol, 1 eq), Pd/C (200 mg, 0.2 eq) and potassium acetate (6.00 g, 61 mmol, 16 eq) in 300 mL of MeOH was stirred for 24 h at room temperature under H2, and then filtered through a Celite pad. The filtrate was concentrated in vacuo and treated with 100 mL of saturated Na2CO3 aqueous solution. The mixture was extracted with CH2Cl2 (50 mL×3). The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the title compound as pale yellow oil (450 mg, 90%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 135.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.95 (2H, m), 3.38 (2H, m), 3.83 (2H, s), 7.08 (1H, m), 8.14 (1H, m), 8.28 (1H, m) ppm.

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated in vacuo
  3. additiontreated with 100 mL of saturated Na2CO3 aqueous solution
  4. extractionThe mixture was extracted with CH2Cl2 (50 mL×3)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a5f761e216747b8a3be21d009fa48fa
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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