Acetic Acid → HCID 57642063, compound

HRID 2112384Notes

Reaction equation

HRID 2112384 reaction equation
N1CC[CH2:3][CH2:2]1.C(O)(=O)C.[CH3:10][CH:11]([N:13]1[C:17]([CH3:18])=[CH:16][C:15](=[O:19])[NH:14]1)[CH3:12].[F:20][C:21]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]>C(O)C>[CH3:10][CH:11]([N:13]1[C:17]([CH3:18])=[C:16]([CH:23]([C:22]2[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:21]=2[F:20])[O:24][CH2:2][CH3:3])[C:15](=[O:19])[NH:14]1)[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 27348732-Fluoro-4-methoxybenzaldehydeHCID 576420625-Methyl-1-(propan-2-yl)-1,2-dihydro-3H-pyrazol-3-one

Product 1

HCID 57642063HCID 57642063, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Pyrrolidine (21 ml; 0.257 mol) and acetic acid (22 ml; 0.385 mol) are added to a mixture of 1,2-dihydro-1-(1-methylethyl)-5-methyl-3H-pyrazol-3-one (180 g; 1.28 mol) and 2-fluoro-4-methoxybenzaldehyde (198 g; 1.28 mol) in ethanol (2.7 L). The suspension is heated to about 50° C. for about 67 h. The reaction mixture is then cooled to approx. 17° C. and filtered. The product is washed with diisopropyl ether (500 ml) and subsequently refluxed with THF (2.5 L). The obtained solution is filtered over a pad of Celite and charcoal. The filtrate is concentrated in vacuo and water (2 L) is added to the suspension which is cooled and filtered. The colourless crystals are dried at 50° C.

Workup

  1. temperatureThe reaction mixture is then cooled to approx. 17° C.
  2. filtrationfiltered
  3. washThe product is washed with diisopropyl ether (500 ml)
  4. temperaturesubsequently refluxed with THF (2.5 L)
  5. filtrationThe obtained solution is filtered over a pad of Celite and charcoal
  6. concentrationThe filtrate is concentrated in vacuo and water (2 L)
  7. additionis added to the suspension which
  8. temperatureis cooled
  9. filtrationfiltered
  10. customThe colourless crystals are dried at 50° C.

Sources & evidence

ORD record
ord-9c218fb77e7b477ab18193f47791bbd1
Source dataset
uspto-grants-2009_04
Patent number
US07524822B2

Reaction notes

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