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Sodium Carbonate → 4-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile

HRID 612159
ノート
印刷プレビュー

反応式

HRID 612159 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].C(=O)([O-])OC.[Cl:25][C:26]1[C:32]([OH:33])=[CH:31][C:29]([NH2:30])=[C:28]([F:34])[CH:27]=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[NH4+]>CO.CC(C)=O.O>[Cl:25][C:26]1[C:32]([OH:33])=[CH:31][C:29]([NH:30][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:28]([F:34])[CH:27]=1
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

10

反応物 6

HCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 1586545-Amino-2-chloro-4-fluorophenolHCID 4585885MethylcarbonateHCID 101298981-EthoxyethanolHCID 224666114-Chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile

生成物 1

HCID 22466624
4-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A mixture of 0.279 g of 4-chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile, 0.22 g of the methyl carbonate of 4-chloro-2-fluoro-5-hydroxy-aniline, and 15 ml of ethoxy-ethanol 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 collected, washed with water, and dried. The solids thus obtained were dissolved in a mixture of 30 ml of methyl alcohol and 20 ml of acetone. To this mixture was added 1.5 ml of 28-30% ammonium hydroxide solution. The mixture was heated at 50° C. for 30 minutes and concentrated. The product was collected, washed with ethyl acetate, and dried to give 0.162 g of 4-(4-chloro-2-fluoro-5-hydroxy-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile as a solid, mp 223-225° C.; mass spectrum (EI, m/e): M 403.0731.

後処理

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried
  6. customThe solids thus obtained
  7. concentrationconcentrated
  8. customThe product was collected
  9. washwashed with ethyl acetate
  10. customdried

出典と根拠

ORDレコード
ord-9b0f59a9c5224ce9a4ece0e856e5b7b3
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06002008

反応ノート

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