Ethyl 2-methylacetoacetate → HCID 178432191、化合物

HRID 1361452ノート

反応式

HRID 1361452 の反応式
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[C:16]([F:19])([F:18])[F:17])=[CH:6][CH:5]=1.[CH3:24][CH:25]([C:31]([CH3:33])=O)[C:26](OCC)=[O:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:33][C:31]1[C:25]([CH3:24])=[C:26]([OH:27])[C:14]2[C:12](=[CH:11][C:10]([C:16]([F:17])([F:18])[F:19])=[C:9]([O:8][C:7]3[CH:20]=[CH:21][C:4]([O:3][C:2]([F:22])([F:23])[F:1])=[CH:5][CH:6]=3)[CH:15]=2)[N:13]=1

参加物

5

反応物 3

HCID 701Ethyl 2-methylacetoacetateHCID 6101p-Toluenesulfonic acidHCID 860948674-(4-Trifluoromethoxyphenoxy)-3-trifluoromethylaniline

生成物 1

HCID 178432191HCID 178432191、化合物収率 41.1%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A solution of 3.4 g of 4-(4-trifluoromethoxyphenoxy)-3-trifluoromethyl-aniline, 2.4 g of ethyl 2-methylacetoacetate, and 0.3 g of p-toluenesulfonic acid dissolved in 100 mL of xylene was heated under reflux for 36 hr. This reaction solution was cooled, and the precipitated crystals were collected by filtration to give 1.73 g of 2,3-dimethyl-4-hydroxy-6-(4-trifluoromethoxyphenoxy)-7-trifluoromethyl-quinoline. The filtrate was concentrated under the reduced pressure to give 2,3-dimethyl-4-hydroxy-6-(4-trifluoromethoxyphenoxy)-5-trifluoromethyl-quinoline. Acetic anhydride (40 mL) was added to 2,3-dimethyl-4-hydroxy-6-(4-trifluoromethoxyphenoxy)-5-trifluoromethyl-quinoline obtained from the filtrate, and the mixture was heated at 120 to 125° C. for one hr. This reaction solution was concentrated under the reduced pressure, ethyl acetate was then added to the concentrate, and the mixture was washed with brine. Thereafter, the solvent was removed under the reduced pressure, and the crude product was purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate) to give 0.35 g of 4-acetoxy-2,3-dimethyl-6-(4-trifluoromethoxyphenoxy)-5-trifluoromethyl-quinoline.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 36 hr
  3. temperatureThis reaction solution was cooled
  4. filtrationthe precipitated crystals were collected by filtration

出典と根拠

ORDレコード
ord-6ab3d22c39704a6c87f18edf495c3fe5
出典データセット
uspto-grants-2011_02
特許番号
US07880006B2

反応ノート

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