2,4-Dichloro-5-methoxyaniline → HCID 178486403, 화합물

HRID 902424

반응식

HRID 902424 반응식
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]

참가 물질

6

반응물 3

HCID 14766362,4-Dichloro-5-methoxyanilineHCID 10176127Pyridinium chlorideHCID 178486400HCID 178486400, 화합물

생성물 1

HCID 178486403HCID 178486403, 화합물수율 65.6%

시약·촉매·용매 2

HCID 8076Glycol monoethyl ether용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60a6da8b028c4c2786b4ea99c997b6e7
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365197B2

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