Sodium Carbonate → 3-(3-Nitropyridin-2-yl)-aniline

HRID 1059915노트

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HRID 1059915 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:8]([C:7]1[C:2]([C:16]2[CH:17]=[C:12]([CH:13]=[CH:14][CH:15]=2)[NH2:11])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 922693-Aminophenylboronic acid

생성물 1

HCID 186676353-(3-Nitropyridin-2-yl)-aniline수율 41.4%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a suspension of 2-chloro-3-nitropyridine (792 mg), 3-aminophenylboronic acid (1.01 g) and tetrakis(triphenylphosphine)-palladium (289 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (6.5 ml). The mixture was stirred at 80° C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. Methanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 3-(3-nitropyridin-2-yl)-aniline (445 mg).

후처리

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionMethanol was added to the residue
  7. filtrationThe precipitate was collected by filtration
  8. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-233c1634705d4155a7914d4c9a97e4ce
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

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