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

HRID 1371497노트

반응식

HRID 1371497 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f6e528e06a244fa9be9c5f3bba3e3f86
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157468B2

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