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

HRID 513684ノート

反応式

HRID 513684 の反応式
[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

参加物

5

反応物 1

HCID 117695548-Nitro-7-quinolinecarboxaldehyde

生成物 1

HCID 110520988-Aminoquinoline-7-carboxaldehyde収率 770.4%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 23925Iron触媒HCID 86584229Acetic acid ethanol water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d0af7041a7fd4111bd6cf442e30d7aa7
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

反応ノート

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