Ethyl (chloroformyl)acetate → HCID 178469635, compound

HRID 706612Notes

Reaction equation

HRID 706612 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.Cl[CH:10]([CH:16]=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[OH:8][C:6]1[CH:5]=[CH:4][N:3]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][N:1]=[C:2]2[CH:7]=1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 178507942HCID 178507942, compound

Product 1

HCID 178469635HCID 178469635, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Aminopyridin-4-ol (3 g, 27 mmol) was dissolved in ethanol (90 mL) in 250 mL round bottom flask. Ethyl 2-chloro-3-oxopropanoate (5% in benzene; 130 mL; Commercial solution from Toronto Research Chemicals Inc.) was added and the mixture refluxed for 10 hours. Reaction was concentrated and triturated with ethyl acetate before drying under high vacuum to give ethyl 7-hydroxyimidazo[1,2-a]pyridine-3-carboxylate as a beige solid (829 mg).

Workup

  1. temperaturethe mixture refluxed for 10 hours
  2. customReaction
  3. concentrationwas concentrated
  4. customtriturated with ethyl acetate
  5. custombefore drying under high vacuum

Sources & evidence

ORD record
ord-2bca9c39f46e4aa396641714f00d3302
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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