Ethyl 2-methylacetoacetate → HCID 178432297, 화합물

HRID 1005941노트

반응식

HRID 1005941 반응식
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([F:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:13][CH:14]([C:20]([CH3:22])=O)[C:15](OCC)=[O:16].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH3:22][C:20]1[C:14]([CH3:13])=[C:15]([OH:16])[C:10]2[C:8](=[C:7]([F:12])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=2)[N:9]=1

참가 물질

5

반응물 3

HCID 701Ethyl 2-methylacetoacetateHCID 8000Boron trifluoride etherateHCID 104646904-Tert-butyl-2-fluoroaniline

생성물 1

HCID 178432297HCID 178432297, 화합물수율 23.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

4-t-Butyl-2-fluoroaniline (4.79 g) prepared according to the above process and ethyl 2-methyl-acetoacetate (4.96 g) were refluxed in toluene (60 ml) in the presence of trifluoroboron etherate (0.3 ml) for 3 hr to obtain a reaction solution. The reaction solution thus obtained was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine and was dried over anhydrous sodium sulfate. The solvent was then removed under the reduced pressure. The reaction product was refluxed in diphenyl ether (80 ml) for one hr and was allowed to stand for cooling. The precipitated product was then collected by filtration under the reduced pressure to give 2,3-dimethyl-6-t-butyl-8-fluoro-4-hydroxyquinoline (compound 1, 1.66 g). 1H-NMR data on this compound in deutro-DMSO (dimethyl sulfoxide) were as shown below.

후처리

  1. customto obtain a reaction solution
  2. customThe reaction solution thus obtained
  3. washwas washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was then removed under the reduced pressure
  6. temperatureThe reaction product was refluxed in diphenyl ether (80 ml) for one hr
  7. temperaturefor cooling
  8. filtrationThe precipitated product was then collected by filtration under the reduced pressure

출처 및 근거

ORD 기록
ord-9f0d6bcbf76641629e3a04a844e35a09
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787557B2

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