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

HRID 1935066노트

반응식

HRID 1935066 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-354aa6072c3d4803a6088ea826195d18
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384051B1

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