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

HRID 1844018ノート

反応式

HRID 1844018 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d0826c698e6b4762a8d24aef6c4ca50c
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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