Cyanuric chloride → 7-FLUORO-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILE

HRID 1837328ノート

反応式

HRID 1837328 の反応式
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]([NH2:14])=O)=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:16][CH3:17].N1C(Cl)=NC(Cl)=NC=1Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]#[N:14])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:16][CH3:17]

参加物

5

反応物 3

HCID 7954Cyanuric chloride2 回HCID 516892Sodium BicarbonateHCID 121507017-Fluoro-1,4-dihydro-6-methoxy-4-oxo-3-quinolinecarboxamide

生成物 1

HCID 121507027-FLUORO-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILE収率 41.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

A mixture of 7-fluoro-6-methoxy-4-oxo-1,4,-dihydro-3-quinolinecarboxamide (700 mg, 3.0 mmol) and cyanuric chloride (341 mg, 1.65 mmol) in 15 mL of N,N,-dimethylformamide is heated at 65° C. for 6 hours then cooled to room temperature and an additional 206 mg of cyanuric chloride is added. The mixture is heated at 65° C. for 4 hours then stirred overnight at room temperature. The reaction mixture is poured into ice water and neutralized with saturated sodium bicarbonate. The solids are collected by filtration washing with water and hexane to provide 610 mg of crude product. Purification by flash column chromatography eluting with a gradient of 3% methanol in dichloromethane to 10% methanol in dichloromethane, provides 272 mg of 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarbonitrile, mp 147-149° C.

後処理

  1. temperaturethen cooled to room temperature
  2. temperatureThe mixture is heated at 65° C. for 4 hours
  3. filtrationThe solids are collected by filtration
  4. washwashing with water and hexane
  5. customto provide 610 mg of crude product
  6. customPurification by flash column chromatography
  7. washeluting with a gradient of 3% methanol in dichloromethane to 10% methanol in dichloromethane

出典と根拠

ORDレコード
ord-3c1bad142b3c4e9794358d566fb1eef7
出典データセット
uspto-grants-2004_08
特許番号
US06780996B2

反応ノート

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