Acetic Acid → 1-acetyl-5-methyl-4-{[4-(propan-2-yloxy)phenyl]methyl}-2,3-dihydro-1H-pyrazol-3-one

HRID 910579Notes

Reaction equation

HRID 910579 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:13](=[O:18])[NH:14][NH:15][C:16]=2[CH3:17])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:25](OC(=O)C)(=[O:27])[CH3:26].C(O)(=O)C>CN(C)C=O.O>[C:25]([N:15]1[C:16]([CH3:17])=[C:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=2)[C:13](=[O:18])[NH:14]1)(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 155423244-(4-Isopropoxybenzyl)-5-methyl-1H-pyrazol-3(2H)-one

Product 1

HCID 673496361-acetyl-5-methyl-4-{[4-(propan-2-yloxy)phenyl]methyl}-2,3-dihydro-1H-pyrazol-3-oneYield 77.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,2-Dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one (1.00 g) was suspended in N,N-dimethyl-formamide (5 mL) at room temperature. In addition, potassium carbonate (0.319 g) was added to the suspension, and the mixture was stirred for 30 minutes. Acetic anhydride (0.412 g) was added to the mixture in a dropwise manner at room temperature. The mixture was stirred at room temperature overnight and at 50° C. for 2 hours. In addition, the mixed solution of glacial acetic acid (0.139 g) and water (5.0 g) was added to the reaction mixture under stirring at room temperature. After confirming the precipitation of the crystals, water (25 g) was added to the mixture. The obtained crystals were collected by filtration, washed with water and dried under reduced pressure to give a white solid of 1-acetyl-1,2-dihydro-4-[(4-isopropoxy-phenyl)methyl]-5-methyl-3H-pyrazol-3-one (0.90 g).

Workup

  1. stirringThe mixture was stirred at room temperature overnight and at 50° C. for 2 hours
  2. stirringunder stirring at room temperature
  3. customthe precipitation of the crystals, water (25 g)
  4. additionwas added to the mixture
  5. filtrationThe obtained crystals were collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-81113d5fc2ed4c338042ea82d48857b1
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

Loading…