Ethyl bromopyruvate → HCID 20368822, compound

HRID 616703Notes

Reaction equation

HRID 616703 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:15])[CH:8]=2)[N:3]=1.Br[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[CH2:13]([O:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:15])[CH:8]=2)[N:3]2[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:1]=[C:2]2[CH:11]=1)[CH3:14]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 20368830HCID 20368830, compound

Product 1

HCID 20368822HCID 20368822, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a single-necked flask were combined, 2.1 g. (0.010 mole) of 2-amino-4-ethoxy-6-fluoroquinoline, 2.1 g. (0.011 mole) ethyl bromopyruvate and 30 ml. of acetone. The mixture was refluxed for two hours, cooled to room temperature and the precipitated solid removed by filtration. The solid was partitioned between chloroform and 1N aqueous potassium hydroxide, the organic layer dried over magnesium sulfate and evaporated to dryness to yield 1.7 g. of crude product. This was dissolved in a small amount of chloroformethanol (95:5 v/v) and chromatographed on a column of 50 g. of 60-200 mesh silica gel (J. T. Baker Co.) eluting with the same solvent. Fractions of 50 ml. each were taken when ultraviolet light absorbing material began to come off the column. Fractions 1 through 8 were combined and evaporated to dryness in vacuo to afford 750 mg. of the title compound as a white solid, which upon crystallization from isopropanol melted at 213.5°-214.5° C.

Workup

  1. customIn a single-necked flask were combined
  2. temperatureThe mixture was refluxed for two hours
  3. customthe precipitated solid removed by filtration
  4. customThe solid was partitioned between chloroform and 1N aqueous potassium hydroxide
  5. dry with materialthe organic layer dried over magnesium sulfate
  6. customevaporated to dryness
  7. customto yield 1.7 g
  8. dissolutionThis was dissolved in a small amount of chloroformethanol (95:5 v/v)
  9. customchromatographed on a column of 50 g
  10. washof 60-200 mesh silica gel (J. T. Baker Co.) eluting with the same solvent
  11. customabsorbing material
  12. customevaporated to dryness in vacuo
  13. customto afford 750 mg
  14. customof the title compound as a white solid, which upon crystallization from isopropanol melted at 213.5°-214.5° C.

Sources & evidence

ORD record
ord-c688dfa9949442ecb2e3862adbe44935
Source dataset
uspto-grants-1978_02
Patent number
US04075343

Reaction notes

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