Hydrochloric Acid → HCID 57749362, compound

HRID 1874510Notes

Reaction equation

HRID 1874510 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[CH:13]=[CH:12][N:11]2[N:14]=[C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[N:16]=[C:10]2[CH:9]=1)([O-])=O.Cl.C(O)C>C(=O)([O-])O.[Na+]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[CH:13]=[CH:12][N:11]2[N:14]=[C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[N:16]=[C:10]2[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 57749388HCID 57749388, compound

Product 1

HCID 57749362HCID 57749362, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of N-[7-(3-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (125 mg, 0.368 mmol), reduced iron (500 mg), concentrated hydrochloric acid (500 μL) and ethanol (5 mL) was stirred under refluxing conditions for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate to give the title compound (40.0 mg, 32%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. filtrationthe residue was collected by filtration
  7. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-2f2e8e6deab44cba99a697611d4232a5
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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