Water → 4-[(6-Chloropyrimidin-4-yl)oxy]-2-fluoroaniline

HRID 492860ノート

反応式

HRID 492860 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[CH:10]=2)[N:5]=[CH:4][N:3]=1.O.[Cl-].[NH4+]>C(O)C.CN(C)C=O.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:7]=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=2)=[CH:10][C:11]=1[F:18]

参加物

7

反応物 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 231535954-Chloro-6-(3-fluoro-4-nitrophenoxy)pyrimidine

生成物 1

HCID 231530834-[(6-Chloropyrimidin-4-yl)oxy]-2-fluoroaniline収率 95%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

After dissolving 4-chloro-6-(3-fluoro-4-nitrophenoxy)pyrimidine (9.726 g) in ethanol (100 ml)-N,N-dimethylformamide (100 ml) at room temperature, water (50 ml), ammonium chloride (20 g) and electrolytic iron powder (10 g) were added and the mixture was stirred for 1 hour at 100° C. The reaction mixture was cooled to room temperature. The insoluble portion was removed using celite prior to washing with ethyl acetate. The filtrate was concentrated under reduced pressure, and then the residue was partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine in that order and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was dried under reduced pressure to provide the title compound (8.204 g, 95%) as pale yellow crystals.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble portion was removed
  3. washto washing with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was partitioned between ethyl acetate and water
  6. washThe separated organic layer was washed with water and brine in that order
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was dried under reduced pressure

出典と根拠

ORDレコード
ord-c23795f5ff5e4e64b80360de2a1a51c4
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

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