Methyl acetoacetate → HCID 178491887, compound

HRID 842024Notes

Reaction equation

HRID 842024 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[C:11]1[C:15]([CH3:16])=[N:14][NH:13][C:12]=1[NH2:17].[C:18](OC)(=O)[CH2:19][C:20](C)=[O:21]>C(O)(=O)C.C(OCC)C>[Cl:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[C:11]1[C:15]([CH3:16])=[N:14][N:13]2[C:20](=[O:21])[CH:19]=[CH:18][NH:17][C:12]=12

Participants

5

Reactant 2

HCID 7757Methyl acetoacetateHCID 178491888HCID 178491888, compound

Product 1

HCID 178491887HCID 178491887, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-(2,6-dichloro-4-methoxy-phenyl)-5-methyl-2H-pyrazol-3-ylamine (10.1 g, 39 mmol) in acetic acid (17 mL) was added methyl acetoacetate. After the mixture was heated at reflux for 3 hours it was cooled and then diluted with diethyl ether (50 mL) to generate a colorless precipitate. The solid was collected by vacuum filtration and washed with additional ether to afford the title compound as a colorless solid (10.3 g, 77%): +APcI MS (M+1)+338; 1H NMR (methanol-d4) δ: 7.14 (s, 2H), 5.68 (s, 1H), 3.86 (s, 3H), 2.30 (s, 3H), 2.16 (s, 3H).

Workup

  1. temperatureAfter the mixture was heated
  2. temperatureat reflux for 3 hours it
  3. temperaturewas cooled
  4. filtrationThe solid was collected by vacuum filtration
  5. washwashed with additional ether

Sources & evidence

ORD record
ord-1edeb6bd177a413581cd05b7551f4e66
Source dataset
uspto-grants-2002_04
Patent number
US06372743B1

Reaction notes

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