硝基苯 → 5-(N,N-diphenylamino)acenaphthene

HRID 1948

反应方程式

HRID 1948 反应方程式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O.NC1C2C3C(CCC=3C=CC=2)=CC=1.[C:36]1([NH:42][C:43]2[C:53]3[C:54]4[C:46]([CH2:47][CH2:48][C:49]=4[CH:50]=[CH:51][CH:52]=3)=[CH:45][CH:44]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>[Cu].C1(C)C=CC=CC=1>[C:2]1([N:42]([C:43]2[C:53]3[C:54]4[C:46]([CH2:47][CH2:48][C:49]=4[CH:50]=[CH:51][CH:52]=3)=[CH:45][CH:44]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

8

反应物 5

HCID 7416硝基苯HCID 11430碳酸钾HCID 11575碘苯HCID 625475-AminoacenaphtheneHCID 1236299N-phenyl-1,2-dihydroacenaphthylen-5-amine

产物 1

HCID 196889195-(N,N-diphenylamino)acenaphthene收率 75.7%

试剂、催化剂与溶剂 2

HCID 23978铜催化剂HCID 1140甲苯溶剂

反应条件

温度
200 °C

实验过程

33.85 g (0.2 mol) of 5-aminoacenaphtthene was mixed with 102.1 g (0.5 mol) of iodo benzene, 1.3 g (0.02 mol) of copper powder, 34.5 g (0.25 mol) of anhydrous potassium carbonate and 100 ml of nitrobenzene, and the mixture was stirred at 200° C. for 26 hours. The reaction was determined to be finished when disappearance of 5-aminoacenaphthene and 5-(N-phenylamino)acenaphthene as an intermediate was identified. 300 ml of toluene was added thereto to dissolve a product, and the resultant mixture was filtrated and concentrated. The concentrated product was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4) to obtain 48.7 g (yield: 75.7%, melting point: 168.5°-170.5° C.) of 5-(N,N-diphenylamino)acenaphthene.

后处理

  1. dissolutionto dissolve a product
  2. filtrationthe resultant mixture was filtrated
  3. concentrationconcentrated
  4. customThe concentrated product was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4)

来源与证据

ORD记录
ord-34a870e6034145a8adf96361ff614be2
来源数据集
uspto-grants-1998_03
专利号
US05728500

关联笔记

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