Water → HCID 22413579, compound

HRID 1721676Notes

Reaction equation

HRID 1721676 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.O>CN(C=O)C>[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[CH2:21][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 22413579HCID 22413579, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-hydroxytetralone, prepared as in step 1, (2.43 g, 15 mmol) and potassium carbonate (2.76 g, 20 mmol) in DMF (65 mL) was added chloromethylquinoline hydrochloride (3.42 g, 16 mmol), and the resulting mixture was stirred at ambient temperature for 24 hours. The reaction mixture was then poured into water (100 mL) and extracted with ethyl acetate (100 mL). The extract was dried with MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5:1 methylene chloride-ethyl acetate to provide 2.3 g 3,4-Dihydro-6-(2-quinolylmethoxy)-1(2H)-naphthalenone.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. dry with materialThe extract was dried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 5:1 methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-dbe3eaf25ac54d9ba0de0d92952db45f
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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