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

HRID 2213736ノート

反応式

HRID 2213736 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-2241d8b284ce4a23b5d2bd3b7668e53b
出典データセット
uspto-grants-2006_09
特許番号
US07105531B2

反応ノート

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