3-Nitrophenol → N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine

HRID 901649

반응식

HRID 901649 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].S([O-])(=O)(=O)C.[CH2:22]([N:24]([CH:27](O)[CH2:28][CH3:29])[CH2:25][CH3:26])[CH3:23]>CN(C=O)C.O>[CH2:22]([N:24]([CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:23]

참가 물질

7

반응물 4

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 85257MethanesulfonateHCID 5256659Diethylamino-propanol

생성물 1

HCID 22012884N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 3-nitrophenol (2 mmol) in DMF (6 mL) at rt, solid potassium carbonate (4 mmol) was added. A solution of the mesylate of N,N-diethylaminopropanol (2.2 mmol) in DMF (2 mL) was then added to the reaction mixture and heated to 80° C. until completion, according to General Procedure Q1, as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was then treated with cold H2O (15 mL), and extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of the solvent in vacuuo afforded the desired N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine. The crude product was used directly for further transformation.

후처리

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (2×15 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent in vacuuo

출처 및 근거

ORD 기록
ord-2f96c797ff5f4ff681bb4e80d8bbafac
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361678B2

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