Sulfuric Acid → HCID 178469635, compound

HRID 706666Notes

Reaction equation

HRID 706666 reaction equation
Cl[C:2]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][O-].[K+].S(=O)(=O)(O)O.[NH2:16][C:17]1[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][N:18]=1>C(O)C>[OH:23][C:21]1[CH:20]=[CH:19][N:18]2[C:2]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][N:16]=[C:17]2[CH:22]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 74089075Potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olateHCID 178507942HCID 178507942, compound

Product 1

HCID 178469635HCID 178469635, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a chilled (0° C.) solution of potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (16.4 g, 86.3 mmol) in concentrated sulfuric acid (43.5 mmol) and ethanol (50 mL) was added 2-aminopyridin-4-ol (3 g, 27 mmol). The resulting mixture was warmed to ambient temperature and refluxed for 10 hours. The reaction was concentrated and suspended in EtOAc. The solids were isolated to afford 829 mg of pure product. The supernatant was concentrated, and subjected to chromatography on silica with 30% EtOAc/Hexanes as eluent to afford a second batch of desired product (5.8 g, 80% purity) as a brown, viscous oil.

Workup

  1. temperaturerefluxed for 10 hours
  2. concentrationThe reaction was concentrated
  3. customThe solids were isolated

Sources & evidence

ORD record
ord-1a02d7f524eb42f692196d702fb7dcce
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…