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

HRID 548442ノート

反応式

HRID 548442 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 30156371-Methoxyethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf09d8a3b5db4ddea2556b6bf3fa2bcf
出典データセット
uspto-grants-2011_05
特許番号
USRE042376E1

反応ノート

読み込み中…