4-Fluorobenzamide → HCID 59601785, compound

HRID 2388136Notes

Reaction equation

HRID 2388136 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Cl[CH:12]([C:17]([CH3:19])=O)[C:13]([O:15][CH3:16])=[O:14]>C(O)C>[CH3:16][O:15][C:13]([C:12]1[O:7][C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[N:8][C:17]=1[CH3:19])=[O:14]

Participants

4

Reactant 2

HCID 715724-FluorobenzamideHCID 107332Methyl 2-chloroacetoacetate

Product 1

HCID 59601785HCID 59601785, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-fluorobenzamide (12 g, 86.3 mmol) and methyl 2-chloroacetoacetate (10.5 mL, 86.3 mmol) in ethanol (120 mL) was refluxed overnight. Subsequently the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic solution was washed with saturated sodium bicarbonate solution and brine, dried, and concentrated in vacuo. The residue was purified by flash chromatography eluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes to give 2.08 g of the title compound as a white solid. MS: (+) m/z 236.2 (M+1).

Workup

  1. concentrationSubsequently the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic solution was washed with saturated sodium bicarbonate solution and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9b10cc3b773d446bb4946bc4225c67d9
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

Loading…