8-Nitro-7-quinolinecarboxaldehyde → 8-Aminoquinoline-7-carboxaldehyde

HRID 513684

반응식

HRID 513684 반응식
[N+:1]([C:4]1[C:5]([CH:14]=[O:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-])=O>Cl.CCO.CC(O)=O.O.[Fe]>[NH2:1][C:4]1[C:5]([CH:14]=[O:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

참가 물질

5

반응물 1

HCID 117695548-Nitro-7-quinolinecarboxaldehyde

생성물 1

HCID 110520988-Aminoquinoline-7-carboxaldehyde수율 770.4%

시약·촉매·용매 3

HCID 313Hydrochloric Acid촉매HCID 23925Iron촉매HCID 86584229Acetic acid ethanol water용매

실험 절차

8-nitroquinoline-7-carbaldehyde 204 (100 mg, 0.49 mmol), iron powder (0.02 ml, 4.95 mmol) and conc. HCl (2 drops) was suspended in a mixture of EtOH/AcOH/water (2:2:1) and the mixture was heated under reflux for 15 min and then stirred at room temperature for 25 min. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with EtOAc and washed with sat. NaHCO3 solution until the pH remained neutral. The organic phase was purified by column chromatography with heptane/EtOAc (80:20) as the eluent to yield the title compound (650 mg, 38%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 min
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residue was diluted with EtOAc
  6. washwashed with sat. NaHCO3 solution until the pH
  7. customThe organic phase was purified by column chromatography with heptane/EtOAc (80:20) as the eluent

출처 및 근거

ORD 기록
ord-d0af7041a7fd4111bd6cf442e30d7aa7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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