Aniline → HCID 68183055, 화합물

HRID 513645노트

반응식

HRID 513645 반응식
[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]

참가 물질

5

반응물 3

HCID 6115AnilineHCID 4311764Sodium borohydrideHCID 117695548-Nitro-7-quinolinecarboxaldehyde2회

생성물 1

HCID 68183055HCID 68183055, 화합물수율 71.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9944d5d4a6124901bbc54a3baa828a32
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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