5-Methoxyindan-1-one → HCID 9947972, compound

HRID 1108985Notes

Reaction equation

HRID 1108985 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2.CC1C=CC(N=[CH:21][C:22]2[C:23]([NH2:31])=[CH:24][C:25]3[O:29][CH2:28][O:27][C:26]=3[CH:30]=2)=CC=1>C(O)C.[OH-].[Na+].C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[C:8]3=[N:31][C:23]4[CH:24]=[C:25]5[O:29][CH2:28][O:27][C:26]5=[CH:30][C:22]=4[CH:21]=[C:7]3[CH2:6][C:5]=2[CH:4]=1

Participants

6

Reactant 2

HCID 787875-Methoxyindan-1-oneHCID 2416176639-66-3

Product 1

HCID 9947972HCID 9947972, compoundYield 134.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

To 5-methoxyindan-1-one (350 mg, 2 mmol) is added 6[[(4-methylphenyl)-imino]methyl]-1,3-benzodioxol-5-amine (512 mg, 1 mmol) in ethanol (4 mL) and 2N sodium hydroxide (1 mL). The reaction mixture is heated at reflux (about 100° C.) for 16 hrs. Upon cooling the reaction product is dissolved in methylene chloride (200 mL) and extracted with a saturated sodium chloride solution (200 mL). The organic layer is dried with a rotatory evaporator. The resulting residue is chromatographed on silica gel with 2:3 ethyl acetate/hexanes to yield 8-Methoxy-10H-1,3-dioxolo[4,5-g]indeno[1,2-b]quinoline (393 mg, 67.4% of theory).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureUpon cooling the reaction product
  3. extractionextracted with a saturated sodium chloride solution (200 mL)
  4. customThe organic layer is dried with a rotatory evaporator
  5. customThe resulting residue is chromatographed on silica gel with 2:3 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c0e1f15e680d4002ab562855900f125f
Source dataset
uspto-grants-1994_06
Patent number
US05318976

Reaction notes

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