Sodium Carbonate → 3,4-Dihydro-2,7-naphthyridin-1(2H)-one

HRID 1818911Notes

Reaction equation

HRID 1818911 reaction equation
COC1C=CC(C[N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:9]1(=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[N:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 112886342-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

Product 1

HCID 111826883,4-Dihydro-2,7-naphthyridin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-methoxy-benzyl)-3,4-dihydro-2H-[2,7]naphtyridine-1-on (1.63 g, 6.075 mmol) was suspended in 30 mL of anhydrous toluene, added with p-toluene sulfonic acid monohydrate (4.62 g, 24.30 mmol) and heated to reflux for about 6 hours under the nitrogen atmosphere. The mixture, while being stirred at 0° C., neutralized by adding a saturated solution of sodium carbonate and extracted seven times with 150 mL of 15% MeOH/MC. The resulting organic layer was dried with anhydrous sodium sulfate, filtered and then concentrated. A silica gel column chromatography (7% MeOH/MC) was performed on the resulting residue an dobtained 550 mg (61%) of 3,4-dihydro-2H-[2,7]naphtyridine-1-on in white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for about 6 hours under the nitrogen atmosphere
  3. extractionextracted seven times with 150 mL of 15% MeOH/MC
  4. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4301ceac529b47e892c3d2ff843dc8bd
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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