Benzyl Bromide → 1-benzyl-4-hydroxy-1,6-naphthyridin-2(1H)-one

HRID 539942Notes

Reaction equation

HRID 539942 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([O:13]C)=O)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[CH2:18]([N:4]1[C:5]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:11]([OH:13])=[CH:2][C:1]1=[O:3])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 66524315Methyl 4-(acetylamino)pyridine-3-carboxylate

Product 1

HCID 712553201-benzyl-4-hydroxy-1,6-naphthyridin-2(1H)-oneYield 26,426.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(acetylamino)pyridine-3-carboxylate (70 g, 0.36 mol) and sodium hydride (50 g, 1.25 mol, 60% in mineral oil) in anhydrous tetrahydrofuran (800 mL) was stirred at room temperature for 30 minutes. To the above mixture was added bromomethylbenzene (60 g, 0.36 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured onto crashed ice (600 mL), concentrated in vacuo, and washed with ethyl acetate (400 mL). The aqueous layer was neutralized by addition of 3 N aqueous solution of hydrochloric acid to pH 7. The formed solid was collected by filtration and dried in vacuo to afford 24 g of 1-benzyl-4-hydroxy-1,6-naphthyridin-2(1H)-one as a pale yellow solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. additionThe reaction mixture was poured
  3. concentrationconcentrated in vacuo
  4. washwashed with ethyl acetate (400 mL)
  5. additionThe aqueous layer was neutralized by addition of 3 N aqueous solution of hydrochloric acid to pH 7
  6. filtrationThe formed solid was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-2a01062b874d444296bd8dd27d24ff6f
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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