3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile

HRID 548442노트

반응식

HRID 548442 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[F:27])[NH2:23]>COC(O)C.C(OCC)(=O)C>[Cl:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:17]#[N:18])[CH:24]=[CH:25][C:26]=1[F:27]

참가 물질

5

반응물 2

HCID 97083-Chloro-4-fluoroanilineHCID 111399754-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

생성물 1

HCID 108940424-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile수율 48.2%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 30156371-Methoxyethanol용매

실험 절차

A mixture of 4.4 g (16.7 mmol) of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile and 2.67 g (18.3 mmol) of 3-chloro-4-fluoro aniline in 110 ml of methoxyethanol was refluxed under nitrogen for 4 hours. The reaction mixture was diluted with ethyl acetate and wash with sodium bicarbonate solution and sodium chloride solution. The organic layer was dried over sodium sulfate and then the solvent was removed under vacuum. The residue was chromatographed on silica gel eluting with mixture of ethyl acetate and methanol to give 3 g yellow solid: mass spectrum (electrospray, m/e): 372.9.

후처리

  1. temperaturewas refluxed under nitrogen for 4 hours
  2. washwash with sodium bicarbonate solution and sodium chloride solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was removed under vacuum
  5. customThe residue was chromatographed on silica gel eluting with mixture of ethyl acetate and methanol

출처 및 근거

ORD 기록
ord-bf09d8a3b5db4ddea2556b6bf3fa2bcf
출처 데이터셋
uspto-grants-2011_05
특허 번호
USRE042376E1

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