Sodium Hydroxide → 8-Quinolinamine, 6-bromo-

HRID 428539

반응식

HRID 428539 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[OH-].[Na+]>CCO.CC(O)=O.O.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 1104636-Bromo-8-nitroquinoline

생성물 1

HCID 936378-Quinolinamine, 6-bromo-수율 905.1%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 86584229Acetic acid ethanol water용매

실험 절차

To a solution of 6-bromo-8-nitro-quinoline (4 g, 1.58 mmol) in EtOH/HOAc/H2O (50 mL/50 mL/25 mL) was added iron metal (3.18 g, 5.69 mmol). The resulting solution was heated at reflux for 3 hours. The cooled reaction mixture was neutralized with 2.5 N NaOH, filtered through celite to remove iron solids and washed with EtOAc. The eluent was extracted into EtOAc (3×200 mL), combined, dried over NASO4 and concentrated. The resulting oil was purified by column chromatography (40% EtOAc/hexanes) affording 3.19 g (91%) of a yellow solid: mp 142-145° C.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 3 hours
  3. customThe cooled reaction mixture
  4. filtrationfiltered through celite
  5. customto remove iron solids
  6. washwashed with EtOAc
  7. extractionThe eluent was extracted into EtOAc (3×200 mL)
  8. customdried over NASO4
  9. concentrationconcentrated
  10. customThe resulting oil was purified by column chromatography (40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-16bb28a504284b7aa752d5c9f8b07163
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313126B1

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