Piperidine → 2-Acetyl-4-nitro-1H-indene-1,3(2H)-dione

HRID 2118416Notes

Reaction equation

HRID 2118416 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]=1[C:13]([OH:15])=O)([O-:3])=[O:2].N1CCCCC1.CC(=O)[CH2:24][C:25](=[O:27])[CH3:26]>N1C=CC=CC=1.CCOCC>[C:25]([CH:26]1[C:13](=[O:15])[C:5]2[C:6](=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[C:7]1=[O:9])(=[O:27])[CH3:24]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 31261AcetylacetoneHCID 690433-Nitrophthalic acid

Product 1

HCID 27352622-Acetyl-4-nitro-1H-indene-1,3(2H)-dioneYield 76.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 100 g of 3-nitrophthalic acid in 100 mL of pyridine was added 0.8 mL of piperdine followed by 500 g of 2,4-pentanedione at room temperature. The mixture was stirred at 35°-40° C. for 6 hours and then diluted with 100 mL ether. The pyridine salt was filtered oft, washed with 100 ml of ether, dried, suspended in waer, and acidified with 400 mL of 6N HCl. The title compound was filtered off, dried,and recrystallized from ethanol to yield 84 g of yellow crystals, m.p. 148°-150°.

Workup

  1. filtrationThe pyridine salt was filtered oft
  2. washwashed with 100 ml of ether
  3. customdried
  4. filtrationThe title compound was filtered off
  5. customdried,and recrystallized from ethanol

Sources & evidence

ORD record
ord-2bbb308dbd0247bfa068e2dbbfa61465
Source dataset
uspto-grants-1987_07
Patent number
US04678499

Reaction notes

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