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5-Methoxy-o-toluidine → 7-Chloro-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile

HRID 2213729
ノート
印刷プレビュー

反応式

HRID 2213729 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:15])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:27])=[C:24]([CH:26]=1)[NH2:25].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Cl:15][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:25][C:24]3[CH:26]=[C:20]([O:19][CH3:18])[CH:21]=[CH:22][C:23]=3[CH3:27])=[C:3]([C:16]#[N:17])[CH:4]=[N:5]2)=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 995005-Methoxy-o-toluidineHCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 219564524,7-Dichloro-6-nitroquinoline-3-carbonitrile

生成物 1

HCID 219563857-Chloro-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile収率 62.1%

試薬・触媒・溶媒 1

HCID 8076
Glycol monoethyl ether
溶媒

反応条件

温度
115 °C

実験手順

A mixture of 0.9 g (3.36 mmol) of 4,7-dichloro-6-nitro-3-quinolinecarbonitrile, 0.55 g (4.0 mmol) of 5-methoxy-2-methylaniline, 0.46 g (4.0 mmol) of pyridine hydrochloride in 10.0 mL of 2-ethoxyethanol is heated at 115° C. for 1 hour, cooled and poured into a saturated solution of sodium bicarbonate. The oil is extracted with methylene chloride, dried over anhydrous sodium sulfate and the solvent is evaporated to yield a foam. This is purified by silica gel chromatography, eluting with methylene chloride/methanol (99.5:0.5) to yield 0.77 g of 7-chloro-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile as a yellow solid, mp 180–182° C.

後処理

  1. temperaturecooled
  2. extractionThe oil is extracted with methylene chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent is evaporated
  5. customto yield a foam
  6. customThis is purified by silica gel chromatography
  7. washeluting with methylene chloride/methanol (99.5:0.5)

出典と根拠

ORDレコード
ord-979c1daccaef4388b6267b8fcb195608
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07105531B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート