Ethyl 2-methylacetoacetate → HCID 178432194, 화합물

HRID 1361459노트

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HRID 1361459 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[NH2:5].[CH3:18][CH:19]([C:25]([CH3:27])=O)[C:20](OCC)=[O:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.ClC1C(C(=O)C2C=CC(Cl)=CC=2)=CC=C2C=1C(O)=C(C)C(C)=N2>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:6]([C:20]([OH:21])=[C:19]([CH3:18])[C:25]([CH3:27])=[N:5]2)=[CH:7][C:8]=1[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 701Ethyl 2-methylacetoacetateHCID 6101p-Toluenesulfonic acidHCID 30165104-Amino-2,4'-dichlorobenzophenoneHCID 178432175HCID 178432175, 화합물

생성물 1

HCID 178432194HCID 178432194, 화합물수율 77%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A solution of 2.7 g of 3-chloro-4-(4-chlorobenzoyl)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 31 hr. This reaction solution was cooled, and the precipitated crystals were collected by filtration and were washed with n-hexane to give 2.68 g of a mixture of 5-chloro-6-(4-chlorobenzoyl)-4-hydroxy-2,3-dimethyl-quinoline with 7-chloro-6-(4-chlorobenzoyl)-4-hydroxy-2,3-dimethyl-quinoline (yield 77%). The crystals of the mixture thus obtained were stirred in 40 mL of acetic anhydride with heating at 120 to 125° C. for one hr. The reaction solution was concentrated, and the crude product was then purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate) to give 1.0 g of 4-acetoxy-5-chloro-6-(4-chlorobenzoyl)-2,3-dimethyl-quinoline (yield 32.6%) and 0.47 g of 4-acetoxy-7-chloro-6-(4-chlorobenzoyl)-2,3-dimethyl-quinoline (yield 15.6%).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 31 hr
  3. temperatureThis reaction solution was cooled
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwere washed with n-hexane

출처 및 근거

ORD 기록
ord-45ff7f3812634f8f814fa60441d29692
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880006B2

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