Sulfuric Acid → HCID 118378922, compound

HRID 931039Notes

Reaction equation

HRID 931039 reaction equation
[Br:1][C:2]1[C:3]([NH2:11])=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:7]=1.Cl[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][O-].[K+].S(=O)(=O)(O)O.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[C:3]2[N:4]([C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:11]=2)[CH:5]=[C:6]([CH:8]2[CH2:9][CH2:10]2)[CH:7]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67334263HCID 67334263, compoundHCID 74089075Potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 118378922HCID 118378922, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-bromo-5-cyclopropylpyridin-2-amine (0.753 g), potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (1.30 g), sulfuric acid (0.208 mL) and ethanol (15 mL) was heated with reflux overnight. The reaction mixture was neutralized with 1N sodium hydroxide at 0° C., and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (565 mg).

Workup

  1. temperaturewas heated
  2. temperaturewith reflux overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b5256a6330484fd9ab56b9ffbb0bbd65
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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