Pyridine → 8-Bromo-1,6-naphthyridine

HRID 992066노트

반응식

HRID 992066 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.[Br:11]Br.N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][C:9]1[CH:8]=[N:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24408BromineHCID 674881,6-Naphthyridine

생성물 1

HCID 8172708-Bromo-1,6-naphthyridine수율 27%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매3회

실험 절차

To a stirred solution of [1,6]-naphthyridine (4.73 g, 36.4 mmol) in CCl4 (200 mL) was added Br2 (2.25 mL, 43.7 mmol) in CCl4 (35 mL) dropwise via an addition funnel. The resulting solution was heated at reflux for 1 hour. Pyridine (2.94 mL, 36.4 mmol) in CCl4 (30 mL) was added dropwise to the refluxing solution, and the mixture was refluxed overnight. The cooled reaction mixture was filtered, and the solids were digested with 1 M NaOH (200 mL) for 1 hour. The basic solution was extracted into CH2Cl2 (2×200 mL), and the organic fractions were combined, dried over Na2SO4 and concentrated. The resulting oil was purified by column chromatography (10% EtOAc/CH2Cl2) affording 2.03 g (27%) of the title compound as yellow crystals: mp 79-81° C.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe mixture was refluxed overnight
  4. customThe cooled reaction mixture
  5. filtrationwas filtered
  6. extractionThe basic solution was extracted into CH2Cl2 (2×200 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe resulting oil was purified by column chromatography (10% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-3a5cd81e10d0428da65b9dc6ea8bfa91
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465482B2

반응 노트

불러오는 중…