Ethyl Acetoacetate → HCID 178429174, compound

HRID 1837400Notes

Reaction equation

HRID 1837400 reaction equation
Cl.[N+:2]([C:5]1[CH:9]=[N:8][NH:7][C:6]=1[NH2:10])([O-:4])=[O:3].[C:11](OCC)(=[O:16])[CH2:12][C:13]([CH3:15])=O>C(O)(=O)C>[N+:2]([C:5]1[CH:9]=[N:8][N:7]2[C:11]([OH:16])=[CH:12][C:13]([CH3:15])=[N:10][C:6]=12)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 22676973HCID 22676973, compound

Product 1

HCID 178429174HCID 178429174, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

50 g of 4-nitro-2H-pyrazol-3-ylamine hydrochloride (prepared in accordance with H. Dorn and H. Dilcher, Liebigs Ann. Chem., 707, 141, 1967) and 60 g of ethyl acetoacetate in 160 cc of acetic acid were introduced into a 500 cc three-necked round-bottomed flask equipped with a magnetic stirrer, a thermometer and a condenser. The reaction medium was refluxed for 12 hours. The precipitate which formed was filtered off at about 90° C. It was washed with diisopropyl ether and dried under vacuum over phosphoric anhydride. This gave 50 g of 3-nitro-5-methylpyrazolo[1,5-a]pyrimidin-7-ol in the form of yellow crystals (yield=84.5%; melting point=290° C. with decomposition), whose elemental analysis, calculated for C7H6N4O3 (MW=194.15 g), was as follows:

Workup

  1. customequipped with a magnetic stirrer
  2. temperatureThe reaction medium was refluxed for 12 hours
  3. customThe precipitate which formed
  4. filtrationwas filtered off at about 90° C
  5. washIt was washed with diisopropyl ether
  6. dry with materialdried under vacuum over phosphoric anhydride

Sources & evidence

ORD record
ord-fec339a4563a4a8d85beb50cf4d61b59
Source dataset
uspto-grants-2004_08
Patent number
US06783557B1

Reaction notes

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