Hydrochloric Acid → 2-[(3,4-dihydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone

HRID 963707Notes

Reaction equation

HRID 963707 reaction equation
CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[C:25]1([CH:31]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:32]2[CH:33]=[CH:34][C:35](=[O:38])[NH:36][N:37]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Br[CH2:46][C:47]1[CH2:48][CH2:49][C:50]2[C:55]([CH:56]=1)=[CH:54][CH:53]=[CH:52][C:51]=2[O:57][CH3:58].Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:58][O:57][C:51]1[CH:52]=[CH:53][CH:54]=[C:55]2[C:50]=1[CH2:49][CH2:48][C:47]([CH2:46][N:36]1[C:35](=[O:38])[CH:34]=[CH:33][C:32]([CH:31]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[N:37]1)=[CH:56]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 539561163-Bromomethyl-1,2-dihydro-8-methoxynaphthaleneHCID 543237696-diphenylmethyl-3(2H)-pyridazinone

Product 1

HCID 701877672-[(3,4-dihydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinoneYield 40.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of potassium tert-butoxide (0.39 g) and 18-crown-6 (0.08 g) in dry N,N-dimethylformamide (4 ml) was added 6-diphenylmethyl-3(2H)-pyridazinone (0.83 g) at room temperature. After ten minutes, 3-bromomethyl-1,2-dihydro-8-methoxynaphthalene (0.80 g) was added to the solution and stirred at the same temperature overnight. The reaction mixture was poured into ethyl acetate and 1N hydrochloric acid and the organic layer was separated, washed with water, aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 2-[(3,4-dihydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.55 g).

Workup

  1. waitAfter ten minutes
  2. customthe organic layer was separated
  3. washwashed with water, aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fc941f8248474a3095e8424107c64fc2
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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