Ammonium Hydroxide → 4-(4-aminophenyl)-1H-pyrrole-3-carboxamide

HRID 734627ノート

反応式

HRID 734627 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([O:15]CC)=O)=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[NH4+:19]>C(OCC)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([NH2:19])=[O:15])=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 14923Ammonium HydroxideHCID 69064082ethyl 4-(4-aminophenyl)-1H-pyrrole-3-carboxylate

生成物 1

HCID 451167614-(4-aminophenyl)-1H-pyrrole-3-carboxamide

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

A suspension of 0.07 g (0.304 mmol) of ethyl 4-(4-aminophenyl)-1H-pyrrole-3-carboxylate in 10 cm3 of a 22% aqueous ammonium hydroxide solution is heated in an autoclave at a temperature in the region of 80° C. for 84 hours. After stopping the heating and then returning to ambient temperature and pressure, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give an orange solid which is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (98/1/1 by volume)]. After concentrating the fractions under reduced pressure, a residue is obtained which is stirred in 10 cm3 of diethyl ether and then filtered and dried under reduced pressure (2.7 kPa) to give 0.02 g of 4-(4-aminophenyl)-1H-pyrrole-3-carboxamide, in the form of a brown solid: EI: m/z=201 (M+) base peak, m/z=185 (M−NH2+), m/z=157 (M-CONH2+).

後処理

  1. customthen returning to ambient temperature
  2. concentrationpressure, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give an orange solid which
  4. customis purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (98/1/1 by volume)]
  5. concentrationAfter concentrating the fractions under reduced pressure
  6. customa residue is obtained which
  7. filtrationfiltered
  8. customdried under reduced pressure (2.7 kPa)

出典と根拠

ORDレコード
ord-f19f91335b8d43d78963a6916eb2069f
出典データセット
uspto-grants-2009_09
特許番号
US07592365B2

反応ノート

読み込み中…