Bromine → 6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

HRID 1371497ノート

反応式

HRID 1371497 の反応式
BrBr.[CH2:3]([N:10]1[CH2:19][CH2:18][C:17]2[NH:16][C:15](=[O:20])[CH2:14][CH2:13][C:12]=2[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)(=O)C>[CH2:3]([N:10]1[CH2:19][CH2:18][C:17]2[NH:16][C:15](=[O:20])[CH:14]=[CH:13][C:12]=2[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

4

反応物 2

HCID 24408BromineHCID 162289266-Benzyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridin-2-one

生成物 1

HCID 223351456-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one収率 44.9%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
100 °C

実験手順

Bromine (750 μl, 14.6 mmol) in glacial acetic acid (5 ml) was added dropwise over 5 minutes to (6-benzyl-3,4,5,6,7,8-hexahydro-1H-[1,6]naphthyridin-2-one (3.37 g, 13.9 mmol) (reference WO9830560) dissolved in glacial acetic acid (50 ml) at 100° C. The mixture was heated at 100° C. for 2.5 hours and then was cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was basified with 10% sodium carbonate solution (50 ml). The aqueous mixture was extracted with chloroform (4×50 ml) and the combined organic solutions were dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using methanol in dichloromethane (gradient from 0:100 to 3:97) to give the title compound as yellow crystals (1.5 g).

後処理

  1. temperaturewas cooled to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. extractionThe aqueous mixture was extracted with chloroform (4×50 ml)
  4. dry with materialthe combined organic solutions were dried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-f6e528e06a244fa9be9c5f3bba3e3f86
出典データセット
uspto-grants-2007_01
特許番号
US07157468B2

反応ノート

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