Acetoacetamide → HCID 76695326, compound

HRID 1868446Notes

Reaction equation

HRID 1868446 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].[C:11]([NH2:17])(=[O:16])[CH2:12][C:13]([CH3:15])=[O:14]>C(O)(C)C.CC(O)=O.N1CCCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:12]([C:13](=[O:14])[CH3:15])[C:11]([NH2:17])=[O:16])=[CH:4][C:3]=1[F:10]

Participants

6

Reactant 2

HCID 80077AcetoacetamideHCID 27249854-Chloro-3-Fluorobenzaldehyde

Product 1

HCID 76695326HCID 76695326, compoundYield 67.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-3-fluorobenzaldehyde (2.47 g, 15.5 mmol), acetoacetamide (1.57 g, 15.5 mmol), AcOH (35 μL, 0.62 mmol) and piperidine (61 μL, 0.62 mmol) in isopropyl alcohol (30 mL) was stirred at room temperature for 2.5 days and evaporated under reduced pressure. The crude product was purified by a silica gel column (120 g) eluting from 50% to 80% EtOAc in hexanes to afford 2-(4-chloro-3-fluorobenzylidene)-3-oxobutanamide (2.54 g, 67.6%) as an off-white solid.

Workup

  1. customevaporated under reduced pressure
  2. customThe crude product was purified by a silica gel column (120 g)
  3. washeluting from 50% to 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-66a11216479d437bb62709802878a84a
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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