Benzylamine → Benzyl-(3-benzyloxy-2-nitro-phenyl)-amine

HRID 730559노트

반응식

HRID 730559 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](F)[C:16]=1[N+:22]([O-:24])=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[CH2:25]([NH:32][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:16]=1[N+:22]([O-:24])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 578349821-(Benzyloxy)-3-fluoro-2-nitrobenzene

생성물 1

HCID 21254743Benzyl-(3-benzyloxy-2-nitro-phenyl)-amine수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
110 °C

실험 절차

Potassium carbonate (5.71 g., 41.4 mmol) was added to a solution of 1-benzyloxy-3-fluoro-2-nitro-benzene (6.818 g, 27.6 mmol) and benzylamine (3.32 mL, 30.34 mmol) in tetrahydrofuran, and the resulting suspension was heated to 110° C. for 2 hours. After cooling to room temperature, the mixture was poured onto 1 L of ice water and extracted twice with 150 mL ethyl acetate and twice with 75 mL dichloromethane. The combined organic fractions were dried over sodium sulfate and concentrated in vacuo in the presence of 25 g. silica gel. The preloaded silica gel was submitted to flash chromatography (8% to 35% ethyl acetate in hexanes) to give 8.118 g (24.28 mmol, 88%) of benzyl-(3-benzyloxy-2-nitro-phenyl)-amine as an orange solid. MS: 335 (M+H)+.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted twice with 150 mL ethyl acetate and twice with 75 mL dichloromethane
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated in vacuo in the presence of 25 g

출처 및 근거

ORD 기록
ord-922b7aaf4a9844d9920e6fbfe9ca6c46
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582760B2

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