Pyridine → HCID 136342831, compound

HRID 5001Notes

Reaction equation

HRID 5001 reaction equation
[OH:1][C:2]1[C:3]([CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH2:15])=[CH:4][C:5]([CH3:12])=[C:6]2[C:10]=1[C:9](=O)[CH2:8][CH2:7]2.Cl.[NH2:23][OH:24].N1C=CC=CC=1>C(O)C.C(OCC)(=O)C>[OH:1][C:2]1[C:3]([CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH2:15])=[CH:4][C:5]([CH3:12])=[C:6]2[C:10]=1[C:9](=[N:23][OH:24])[CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 136559222,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one

Product 1

HCID 136342831HCID 136342831, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

An ethanol solution containing 120 g of 2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one, 45 of hydroxylamine hydrochloride and 200 ml of pyridine in 1,200 ml of ethanol was refluxed for 4 hours. After the reaction was completed, the reaction mixture was concentrated to dryness under a reduced pressure, then the residue thus obtained was dissolved in 2 liters of ethyl acetate and washed three times with 1 liter of water each time, and the residue was dried again under a reduced pressure. Recrystallized from ethyl acetate/n-hexane mixture to obtain 90 g of 2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one oxime. Light yellow flake-like crystals. Melting point: 146° C. (Decomposed).

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationthe reaction mixture was concentrated to dryness under a reduced pressure
  3. customthe residue thus obtained
  4. washwashed three times with 1 liter of water each time
  5. customthe residue was dried again under a reduced pressure
  6. customRecrystallized from ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-8a19649ebcff469e91efc72f600ed2a4
Source dataset
uspto-grants-1993_09
Patent number
US05242919

Reaction notes

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