Ethyl 2-methylacetoacetate → HCID 178432191, 화합물

HRID 1361452노트

반응식

HRID 1361452 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178432191HCID 178432191, 화합물수율 41.1%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6ab3d22c39704a6c87f18edf495c3fe5
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880006B2

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