3-Bromoaniline → 8-(3-Bromo-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile

HRID 989301ノート

反応式

HRID 989301 の反応式
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[N:12]=[CH:13][N:14]=[C:8]3[CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[CH:10]=[C:9]4[N:12]=[CH:13][N:14]=[C:8]4[CH2:7][C:6]=3[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][CH:24]=1

参加物

6

反応物 4

HCID 115623-BromoanilineHCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 693728438-Chloroimidazo[4,5-g]quinoline-7-carbonitrile

生成物 1

HCID 693732468-(3-Bromo-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile収率 63.1%

試薬・触媒・溶媒 1

HCID 8076Glycol monoethyl ether溶媒

実験手順

A mixture of 0.2 g (0.87 mmol) of 8-chloroimidazo[4,5-g]quinoline-7-carbonitrile, 0.12 mL (1.1 mmol) of 3-bromoaniline, and 0.1 g (0.87 mmol) of pyridine hydrochloride in 5.0 mL of 2-ethoxyethanol is heated at reflux temperature for 45 minutes, then cooled to room temperature. The product mixture is poured into a saturated solution of sodium bicarbonate and stirred for 0.5 hour. The solid is collected by filtration, washed with water and dried. The solid is purified by silica gel chromatography, utilizing a gradient of methylene chloride/methanol(98:2 to 93:7) to yield 0.20 g of 8-(3-bromo-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile as pink solid, mp 286-288° C.

後処理

  1. temperatureis heated
  2. temperatureat reflux temperature for 45 minutes
  3. filtrationThe solid is collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe solid is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-32fedfaad3874e4e8a9f552f112807f7
出典データセット
uspto-grants-2003_10
特許番号
US06638929B2

反応ノート

読み込み中…