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

HRID 730559ノート

反応式

HRID 730559 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
110 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-922b7aaf4a9844d9920e6fbfe9ca6c46
出典データセット
uspto-grants-2009_09
特許番号
US07582760B2

反応ノート

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