Acetic Acid → HCID 367454, compound

HRID 382765Notes

Reaction equation

HRID 382765 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)([O-:10])=[O:9].N1CCCCC1.CC(O)=O>C(O)(C)C>[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[C:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 8082PiperidineHCID 31261Acetylacetone

Product 1

HCID 367454HCID 367454, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of pentane-2,4-dione (20.0 g, 200 mmol), 4-nitrobenzaldehyde (30.2 g, 200 mmol), piperidine (1.70 g, 20.0 mmol), and HOAc (1.20 g, 20.0 mmol) in 500 mL of isopropanol were heated with a heat gun until a homogeneous solution resulted. The reaction mixture was then stirred at room temperature for 18 hours. The precipitated solids were filtered, sequentially washed with isopropanol and ether, and air dried to give 28.3 g of the title compound. The filtrate also yielded 5.10 g of 3-(4-nitrophenyl)methylenopentane-2,4-dione for a combined yield of 72%: mp 90-91° C. The product was used in the next step after spectral characterization.

Workup

  1. temperaturewere heated with a heat gun until a homogeneous solution
  2. customresulted
  3. filtrationThe precipitated solids were filtered
  4. washsequentially washed with isopropanol and ether, and air
  5. customdried

Sources & evidence

ORD record
ord-f3a75535c21c40e8bc460cb09bd9570f
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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