Ethanol → HCID 22605344, compound

HRID 241945Notes

Reaction equation

HRID 241945 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]2[N:8]=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=[C:3]12.S(=O)(=O)(O)O.[CH3:19][CH2:20]O>>[CH2:19]([O:12][C:11]([C:9]1[CH:10]=[C:3]2[C:2](=[O:1])[CH2:7][CH2:6][CH2:5][N:4]2[N:8]=1)=[O:13])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 226053224-oxo-4H,5H,6H,7H-pyrazolo[1,5-a]pyridine-2- carboxylic acid

Product 1

HCID 22605344HCID 22605344, compound

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridine-2-carboxylic acid (16 g, 89 mmol) in 170 mL EtOH is added slowly 12 mL concentrated sulphuric acid and the reaction mixture is heated to 100° C. for 2 h. The reaction mixture is cooled to RT and concentrated under reduced pressure. The residue is poured on ice, neutralized by the addition of an aqueous saturated solution of NaHCO3 and extracted with DCM. The combined organic phases are washed with water and brine, dried on MgSO4 and the solvent are removed under reduced pressure. Yield: 17 g. HPLC-MS: Rt=1.79 min, (M+H)+=209.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is poured on ice
  4. additionneutralized by the addition of an aqueous saturated solution of NaHCO3
  5. extractionextracted with DCM
  6. washThe combined organic phases are washed with water and brine
  7. customdried on MgSO4
  8. customthe solvent are removed under reduced pressure

Sources & evidence

ORD record
ord-bb6ab8a4eed7468b98a5a508a2f53c11
Source dataset
uspto-grants-2014_02
Patent number
US08653097B2

Reaction notes

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