Aniline → HCID 68183055、化合物

HRID 513645ノート

反応式

HRID 513645 の反応式
[N+:1]([C:4]1[C:5]([CH:14]=O)=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+]>CO>[N+:1]([C:4]1[C:5]([CH2:14][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 6115AnilineHCID 4311764Sodium borohydrideHCID 117695548-Nitro-7-quinolinecarboxaldehyde2 回

生成物 1

HCID 68183055HCID 68183055、化合物収率 71.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 8-nitro-quinoline-7-carbaldehyde (Intermediate 204) (500 mg, 2.4 mmol) and aniline (270 μl, 2.9 mmol) in MeOH (20 ml) under a nitrogen atmosphere was stirred at room temperature for 16 hours. Sodium borohydride (269 mg, 7.1 mmol) was added and stirring continued at room temperature for 1 h. The reaction mixture was concentrated in vacuo and residue was diluted with sat. NaHCO3 solution (30 ml) and was extracted with DCM. The organic phases were dried (MgSO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc gradient elution to give the title compound (0.48 g, 69%).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo and residue
  2. additionwas diluted with sat. NaHCO3 solution (30 ml)
  3. extractionwas extracted with DCM
  4. dry with materialThe organic phases were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with heptane/EtOAc gradient elution

出典と根拠

ORDレコード
ord-9944d5d4a6124901bbc54a3baa828a32
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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