Ethyl 2-methylacetoacetate → HCID 178432297, compound

HRID 1005941Notes

Reaction equation

HRID 1005941 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 178432297HCID 178432297, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9f0d6bcbf76641629e3a04a844e35a09
Source dataset
uspto-grants-2004_09
Patent number
US06787557B2

Reaction notes

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