Sodium Carbonate → Ethyl 6-(2,4-dichlorophenyl)-4-oxo-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carboxylate

HRID 57670Notes

Reaction equation

HRID 57670 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][N:11]1[C:15]([C:16](OCC)=[O:17])=[CH:14][C:13]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:12]1.C([O-])(=O)C.[NH4+:31].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:31][C:16](=[O:17])[C:15]2[N:11]([N:12]=[C:13]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 517165Ammonium AcetateHCID 58169992Diethyl 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 58170089Ethyl 6-(2,4-dichlorophenyl)-4-oxo-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9.5 g (23.7 mmol) of diethyl 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-pyrazole-3,5-dicarboxylate (Example 10A) were dissolved in 300 ml of glacial acetic acid, and 18.3 g (237 mmol) of ammonium acetate were added. The mixture was stirred at reflux for 12 h. The reaction mixture was poured into ice-water and neutralized with sodium carbonate. The precipitate was filtered off and dried under high vacuum. This gave 6.86 g (82% of theory) of the product as a solid.

Workup

  1. temperatureat reflux for 12 h
  2. filtrationThe precipitate was filtered off
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-8bcaf9bed6e74ba1a6261fbc7b0171ad
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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