p-Toluenesulfonic acid → 3,4-Dihydro-2,6-naphthyridin-1(2H)-one

HRID 1844018노트

반응식

HRID 1844018 반응식
COC1C=CC(C[N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[N:13][CH:14]=3)[C:9]2=[O:18])=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:9]1(=[O:18])[C:10]2[C:15](=[CH:14][N:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 735546032-(4-Methoxybenzyl)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

생성물 1

HCID 122519733,4-Dihydro-2,6-naphthyridin-1(2H)-one수율 27.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

2-(4-Methoxybenzyl)-3,4-dihydro-2,6-naphthyridin-1(2H)-one (I-67g: 300 mg, 1.119 mmol) was reacted with p-toluene sulfonic acid (851 mg, 4.476 mmol) and toluene (10 mL) at 110° C. for 4 hours. The reaction mass was concentrated under reduced pressure, neutralized with 1N HCl solution to pH 7 and extracted using DCM. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 45 mg of the product (27.10% yield).

후처리

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. extractionextracted
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

출처 및 근거

ORD 기록
ord-d0826c698e6b4762a8d24aef6c4ca50c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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