Ethyl Acetoacetate → HCID 178439525, compound

HRID 48192Notes

Reaction equation

HRID 48192 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]=1[CH2:12][CH2:13][CH3:14].[C:15](OCC)(=[O:20])[CH2:16][C:17]([CH3:19])=O>C(O)(=O)C>[CH3:19][C:17]1[NH:1][C:2]2[N:6]([N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]=2[CH2:12][CH2:13][CH3:14])[C:15](=[O:20])[CH:16]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 178439526HCID 178439526, compound

Product 1

HCID 178439525HCID 178439525, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 11.5 g of ethyl 5-amino-4-propylpyrazole-3-carboxylate, 11.3 g of ethyl acetoacetate, and 100 mL of acetic acid is refluxed overnight. The solvent is removed in vacuo, and the residue triturated with hexane/ether (1:1) to give 14.8 g of off-white solid. 1H NMR (CD3OD) δ: 0.97 (t, 3H), 1.40 (t, 3H), 1.61 (m, 2H), 2.42 (s, 3H), 2.85 (t, 2H), 4.40 (q, 2H), 5.73 (s, 1H). LC-MS (APCI, m/z): 264 (M+1).

Workup

  1. temperatureis refluxed overnight
  2. customThe solvent is removed in vacuo
  3. customthe residue triturated with hexane/ether (1:1)

Sources & evidence

ORD record
ord-d0987a53a2c24d9d9b1147d094e3738b
Source dataset
uspto-grants-2004_03
Patent number
US06703393B2

Reaction notes

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