2,4-Dichloro-5-methoxyaniline → HCID 178486403、化合物

HRID 902424ノート

反応式

HRID 902424 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([OH:16])[C:13]([O:17][CH3:18])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20].[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[C:26]([O:30][CH3:31])=[CH:25][C:23]=1[NH2:24].Cl.N1C=CC=CC=1>C(OCCO)C.C(=O)(O)[O-].[Na+]>[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[C:26]([O:30][CH3:31])=[CH:25][C:23]=1[NH:24][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([OH:16])[C:13]([O:17][CH3:18])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20]

参加物

6

反応物 3

HCID 14766362,4-Dichloro-5-methoxyanilineHCID 10176127Pyridinium chlorideHCID 178486400HCID 178486400、化合物

生成物 1

HCID 178486403HCID 178486403、化合物収率 65.6%

試薬・触媒・溶媒 2

HCID 8076Glycol monoethyl ether溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
120 °C

実験手順

A mixture of 0.7 g (2.46 mmol) of 4-chloro-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile, 0.57 g (2.95 mmol) of 2,4-dichloro-5-methoxyaniline and 0.28 g (2.46 mmol) of pyridine hydrochloride in 7 mL of 2-ethoxyethanol is heated at 120° C. for 2 hours, then cooled to room temperature. The product mixture is diluted with saturated solution of sodium bicarbonate and stirred for 15 minutes. The resulting solid is collected by filtration, washed with water and dried. The crude product is purified by silica gel chromatography, utilizing a 98:2 to 90:10 gradient of methylene chloride/methanol to give 0.71 g of 4-(2,4-dichloro-5-methoxyphenylamino)-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile as a yellow solid, mp, 238-240° C.

後処理

  1. temperaturecooled to room temperature
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe crude product is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-60a6da8b028c4c2786b4ea99c997b6e7
出典データセット
uspto-grants-2008_04
特許番号
US07365197B2

反応ノート

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