Ammonia → HCID 17985472, compound

HRID 557210Notes

Reaction equation

HRID 557210 reaction equation
[N:1]1[CH:2]=[C:3]([CH2:10][C:11]([O:13]CC)=O)[N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=12.[NH3:16]>CO>[N:1]1[CH:2]=[C:3]([CH2:10][C:11]([NH2:16])=[O:13])[N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=12

Participants

4

Reactant 2

HCID 222AmmoniaHCID 17985631HCID 17985631, compound

Product 1

HCID 17985472HCID 17985472, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogenate a mixture 2-(imidazo[1,2-a]pyridin-3-yl)acetamide (0.64 gm) and 0.158 gm platinum oxide in 200 mL ethanol saturated with hydrogen chloride at 60 p.s.i. for 2 hours at room temperature. Filter the reaction mixture and concentrate the filtrate under reduced pressure to provide 0.58 gm ethyl 2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-3-yl)acetate. Heat a solution of this ester in 40 mL 2 M ammonia in methanol in a sealed tube at 100° C. for 2 hours. Cool the reaction mixture to room temperature and concentrate under reduced pressure to a volume of about 5 mL. Dilute with ethyl acetate and filter the resulting solid to provide the title compound.

Workup

  1. concentrationconcentrate under reduced pressure to a volume of about 5 mL
  2. additionDilute with ethyl acetate
  3. filtrationfilter the resulting solid

Sources & evidence

ORD record
ord-6b15be029b10404cb102bef9d14a0f74
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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