Acetic Acid → HCID 21984600, compound

HRID 9230Notes

Reaction equation

HRID 9230 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[C:12]1[N:17]2[N:18]=[C:19]([CH2:24][CH3:25])[C:20]([N+:21]([O-])=O)=[C:16]2[CH:15]=[CH:14][CH:13]=1.C(O)(=O)C>C(O)C.O.[Zn]>[CH3:11][O:10][C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C:12]1[N:17]2[N:18]=[C:19]([CH2:24][CH3:25])[C:20]([NH2:21])=[C:16]2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 21984618HCID 21984618, compound

Product 1

HCID 21984600HCID 21984600, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

After dissolving 7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (600 mg) in a mixture of ethanol (30 mL) and water (30 mL), acetic acid (3 mL) and zinc powder (600 mg) were added and the mixture was stirred at 60° C. for 2 hours. The ethanol of the obtained reaction mixture was distilled off under reduced pressure, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the residue and extraction was performed with ethyl acetate. The obtained organic layers were combined, washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 7-(2,6-dimethoxy-4-methylphenyl)-2-ethylpyrazolo[1,5-a]pyridine-3-amine (500 mg) as a crude product.

Workup

  1. additionwere added
  2. distillationwas distilled off under reduced pressure
  3. additionsaturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the residue and extraction
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a6c0895ec1c047d8b96e9207f20ccfd8
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Reaction notes

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