Ethyl 4-chloroacetoacetate → HCID 12269134, compound

HRID 601685Notes

Reaction equation

HRID 601685 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6](=O)[CH2:7]Cl)[CH3:2].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1>C(O)C>[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]1[N:11]=[C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]2[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 706222-Amino-5-bromopyridine

Product 1

HCID 12269134HCID 12269134, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.90 ml of ethyl4-chloro-3-oxobutanoate was dissolved in 50 ml of ethanol, 5.19 g of 2-amino-5-bromopyridine was added, and the mixture was stirred all night by heating under reflux. After cooling down to room temperature, the solvents were distilled outunder reduced pressure, and then, ethyl acetate followed by saturated sodium bicarbonate aqueous solution were added. Organic layer was dried with anhydrous sodium sulfate, and the solvents were distilled outunder reduced pressure. The obtained residues were purified by preparative thin-layer chromatography (hexane:ethyl acetate=60:40) to obtain 9.49 mg of the above compound as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. distillationthe solvents were distilled outunder reduced pressure
  4. additionwere added
  5. dry with materialOrganic layer was dried with anhydrous sodium sulfate
  6. distillationthe solvents were distilled outunder reduced pressure
  7. customThe obtained residues were purified by preparative thin-layer chromatography (hexane:ethyl acetate=60:40)

Sources & evidence

ORD record
ord-0ca75aa2738a4ef5a2eaa46384bb3da2
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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