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

HRID 539942

반응식

HRID 539942 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2a01062b874d444296bd8dd27d24ff6f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871756B2

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