Benzyl Bromide → 1,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(phenylmethyl)-

HRID 249313노트

반응식

HRID 249313 반응식
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+]>C(#N)C>[CH2:11]([N:7]1[CH2:8][CH2:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 674881,6-Naphthyridine2회HCID 4311764Sodium borohydride

생성물 1

HCID 30587131,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(phenylmethyl)-수율 51.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1,6Naphthyridine (13.7 g, 105 mmol) and benzyl bromide (36.05 g, 210 mmol) were combined in acetonitrile (200 ml) and heated to reflux until no 1,6-naphthyridine was visible by thin layer chromatography. After removal of the solvent in vacuo, the residue was washed several times with ether and dissolved in methanol (700 ml). Water (250 ml) was added, and the solution cooled to 0°; portionwise addition of sodium borohydride (20.8 g, 550 mmol) brought about vigorous gas evolution and a slight rise in temperature. The reaction mixture was allowed to warm to room temperature and stir for 18 hours. The solvent was then removed in vacuo and the residue partitioned between water (750 ml) and methylene chloride (300 ml). The aqueous layer was extracted with additional methylene chloride (2×300 ml) and the combined organic extracts were washed once with water and once with saturated aqueous sodium chloride. Removal of solvent provided a dark amber foam, which was purified by column chromatography (99:1 methylene chloride:methanol) to yield the title product (12.1 g, 54 mmol, 51% yield).

후처리

  1. temperatureheated
  2. customAfter removal of the solvent in vacuo
  3. washthe residue was washed several times with ether
  4. dissolutiondissolved in methanol (700 ml)
  5. additionWater (250 ml) was added
  6. temperaturethe solution cooled to 0°
  7. customThe solvent was then removed in vacuo
  8. customthe residue partitioned between water (750 ml) and methylene chloride (300 ml)
  9. extractionThe aqueous layer was extracted with additional methylene chloride (2×300 ml)
  10. washthe combined organic extracts were washed once with water and once with saturated aqueous sodium chloride
  11. customRemoval of solvent
  12. customprovided a dark amber foam, which
  13. customwas purified by column chromatography (99:1 methylene chloride:methanol)

출처 및 근거

ORD 기록
ord-cfedb20691c647bd837fa2492a1f81e7
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05214051

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