4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-6-nitro-quinoline-3-carbonitrile → 6-Amino-4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-quinoline-3-carbonitrile

HRID 1595820

反応式

HRID 1595820 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N+:26]([O-])=O)[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[NH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([C:29]#[N:30])=[C:16]2[NH:15][C:4]1[CH:5]=[CH:6][C:7]([S:8][C:9]2[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=2)=[C:2]([Cl:1])[CH:3]=1

参加物

4

反応物 2

HCID 699572994-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-6-nitro-quinoline-3-carbonitrileHCID 85782573Tin tetrachloride dihydrate

生成物 1

HCID 101360586-Amino-4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-quinoline-3-carbonitrile収率 53.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 5.734 g (13.1 mmol) 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-6-nitro-quinoline-3-carbonitrile, 250 ml ethanol, and 14.83 g (65.6 mmol) tin chloride dihydrate was heated to reflux under N2. Removed heat at 2½ hours and added a large volume of ice water. Made basic with sodium bicarbonate and stirred for 2 hours. With mixture still basic, extracted with chloroform, stirred organic layer with Darco, dried with sodium sulfate and filtered. Stripped solvent and dried in vacuo, giving 2.86 g of yellow-brown solid: mass spectrum (electrospray m/e): M+H=407.3, 409.3.

後処理

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 2½ hours
  5. additionadded a large volume of ice water
  6. extractionWith mixture still basic, extracted with chloroform
  7. stirringstirred organic layer with Darco
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. customStripped solvent and dried in vacuo

出典と根拠

ORDレコード
ord-a5d94fdf01c148dc9754b77e46103e18
出典データセット
uspto-grants-2001_09
特許番号
US06288082B1

関連ノート

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