Sodium Carbonate → 4-(4-Chloro-2-fluoro-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile

HRID 1935066ノート

反応式

HRID 1935066 の反応式
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[C:23]([F:28])[CH:22]=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:2]2[C:11]3[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])=[C:23]([F:28])[CH:22]=1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 938984-Chloro-2-fluoroanilineHCID 101298981-EthoxyethanolHCID 224666114-Chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile

生成物 1

HCID 224667464-(4-Chloro-2-fluoro-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile収率 67.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 0.279 g of 4-chloro-6,7,8trimethoxy-quinoline-3-carbonitrile, 0.177 g of 4-chloro-2-fluoroaniline, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 100 ml of water. To this mixture was added sodium carbonate to pH 9. The product was extracted with ethyl acetate, washed with water, dried and concentrated in vacuo. The solid thus obtained was chromatographed on silica gel eluting with hexanes-ethyl acetate 9:1 to 2:1. Solvent was removed from product fractions giving 0.261 g of 4-(4-chloro-2-fluoro-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile as a yellow solid: mp 166-168° C.; mass spectrum (EI, m/e): M 387.0777.

後処理

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe solid thus obtained
  8. customwas chromatographed on silica gel eluting with hexanes-ethyl acetate 9:1 to 2:1
  9. customSolvent was removed from product fractions

出典と根拠

ORDレコード
ord-354aa6072c3d4803a6088ea826195d18
出典データセット
uspto-grants-2002_05
特許番号
US06384051B1

反応ノート

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