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

HRID 1251959Notes

Reaction equation

HRID 1251959 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 off, washed with 100 ml of ether, dried, suspended in water, 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 off
  2. washwashed with 100 ml of ether
  3. customdried
  4. filtrationThe title compound was filtered off
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-77e7a90605d64db68defc29f11898620
Source dataset
uspto-grants-1988_05
Patent number
US04741765

Reaction notes

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