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Potassium Carbonate → 5-Phenyl-5,6-dihydrophenanthridine

HRID 523446
ノート
印刷プレビュー

反応式

HRID 523446 の反応式
Br[C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Br-].C([N+](C)(C)C)C1C=CC=CC=1.CC(O)=O.CC(O)=O.[Pd]>[C:6]1([N:5]2[CH2:4][C:3]3[C:18](=[CH:19][CH:20]=[CH:21][CH:2]=3)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]2=3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 11430Potassium CarbonateHCID 85712531(2-Bromobenzyl)diphenylamine

生成物 1

HCID 143377485-Phenyl-5,6-dihydrophenanthridine

試薬・触媒・溶媒 3

HCID 21449Benzyltrimethylammonium bromide触媒HCID 4144353Palladium (II) acetate触媒HCID 6228Dimethylformamide
溶媒

反応条件

温度
120 °C

実験手順

10 g (0.295 mol) of (2-bromobenzyl)diphenylamine are dissolved in 500 ml of dimethylformamide under protective atmosphere. 3.4 g (0.075 mol) of benzyltrimethylammonium bromide and 6.1 g (0.443 mol) of potassium carbonate are added to this solution. 0.99 g (0.004 mol) of Pd(OAC)2 is subsequently added under protective gas, and the mixture is stirred at 120° C. for 9 h. After this time, the reaction mixture is cooled to room temperature and extracted with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is recrystallised from n-heptane. The yield is 6 g (80%).

後処理

  1. temperatureAfter this time, the reaction mixture is cooled to room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. customevaporated
  5. customThe residue is recrystallised from n-heptane

出典と根拠

ORDレコード
ord-495a6adf76a44be8ab73ccc2176b0f05
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09337430B2

反応ノート

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