1,3-Indandione → HCID 19042737, compound

HRID 1683151Notes

Reaction equation

HRID 1683151 reaction equation
[NH2:1][C:2]([CH3:7])=[CH:3][C:4](=O)[CH3:5].[C:8]1(=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=O)[CH2:9]1.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:7][C:2]1[N:1]=[C:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8](=[O:18])[C:9]2=[C:4]([CH3:5])[CH:3]=1

Participants

5

Reactant 3

HCID 118151,3-IndandioneHCID 1368734-Amino-3-penten-2-oneHCID 517165Ammonium Acetate

Product 1

HCID 19042737HCID 19042737, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 23.6 g (0.24 mol) of 4-amino-3-penten-2-one, 29.2 g (0.2 mol) of indene-1,3-(2H)dione and 7.7 g (0.1 mol) of ammonium acetate in 500 ml of acetic acid was stirred at 115° C. for 3 hours and concentrated under reduced pressure, and the residue was treated with 500 ml of water and rendered alkaline with solid potassium carbonate. The mixture was extracted three times with methylene chloride, and the combined extracts were washed with 100 ml of water and concentrated under reduced pressure. The residue was crystallized at +5° C. using 20 ml of diethyl ether. 10.2 g of 2,4-dimethyl-5H-indeno[3,2-b]pyridin-5- one were obtained as slightly yellow crystals of m.p. 102°-104° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionthe residue was treated with 500 ml of water
  3. extractionThe mixture was extracted three times with methylene chloride
  4. washthe combined extracts were washed with 100 ml of water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized at +5° C.

Sources & evidence

ORD record
ord-27f4edfdf6ba4e37b0de04d35c828027
Source dataset
uspto-grants-1997_06
Patent number
US05637554

Reaction notes

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