4-Nitrobenzaldehyde → 9-(4-Nitrostyryl)acridine

HRID 1354566ノート

反応式

HRID 1354566 の反応式
[CH3:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)([O-:18])=[O:17]>O1CCCC1.O.[Cl-].[Zn+2].[Cl-]>[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[CH:1][C:2]2[C:15]3[C:10]([N:9]=[C:8]4[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]4)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:21][CH:20]=1)([O-:18])=[O:17]

参加物

6

反応物 2

HCID 5414-NitrobenzaldehydeHCID 119139-Methylacridine

生成物 1

HCID 730989559-(4-Nitrostyryl)acridine収率 35%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
130 °C

実験手順

A mixture of 9-methylacridine (4.83 g, 25.0 mmol), 4-nitrobenzaldehyde (4.23 g, 31.25 mmol) and zinc chloride (5.06 g, 31.25 mmol) is heated at 130° C. for 3 hours with an oil bath. The solid recovered is heated in a solution of sodium metabisulfite in order to eliminate the excess aldehyde and the hot mixture is filtered. Precipitates obtained are dissolved in a minimum amount of tetrahydrofuran and water is added to the solution so as to obtain the product in the form of precipitates. These precipitates are recovered by filtration and dried. The product can be recrystallized from ethanol. The yield is 35%.

後処理

  1. customThe solid recovered
  2. temperatureis heated in a solution of sodium metabisulfite in order
  3. filtrationthe hot mixture is filtered
  4. customPrecipitates
  5. customobtained
  6. additionis added to the solution so as
  7. customto obtain the product in the form
  8. customof precipitates
  9. filtrationThese precipitates are recovered by filtration
  10. customdried
  11. customThe product can be recrystallized from ethanol

出典と根拠

ORDレコード
ord-6365a65917e243f8801d5fc57c5ecc48
出典データセット
uspto-grants-2007_05
特許番号
US07223865B2

反応ノート

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