Sodium Hydroxide → 2-[(1,2,3,4-tetrahydro-5-carboxymethoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone

HRID 344035Notes

Reaction equation

HRID 344035 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH:12]([CH2:18][N:19]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]([CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:20]1)[CH2:13]2)=[O:5])C.[OH-].[Na+]>COCCOC>[C:4]([CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH:12]([CH2:18][N:19]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]([CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:20]1)[CH2:13]2)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 701875372-[(1,2,3,4-tetrahydro-5-ethoxycarbonylmethoxy-2-naphthyi)methyl]-6-diphenylmethyl-3(2H)-pyridazinone

Product 1

HCID 591452362-[(1,2,3,4-tetrahydro-5-carboxymethoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinoneYield 81.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-[(1,2,3,4-tetrahydro-5-ethoxycarbonylmethoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.43 g) in 1,2-dimethoxyethane (9.0 ml) and 1.0N aqueous solution of sodium hydroxide (0.85 ml) was stirred at room temperature For 5 hours. The solution was evaporated in vacuo and extracted with ethyl acetate and 1N hydrochloric acid. The organic layer was separated and washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was crystallized from n-hexane, ethyl acetate and ether to give 2-[(1,2,3,4-tetrahydro-5-carboxymethoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (330 mg) as a white powder.

Workup

  1. customThe solution was evaporated in vacuo
  2. extractionextracted with ethyl acetate and 1N hydrochloric acid
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was crystallized from n-hexane, ethyl acetate and ether

Sources & evidence

ORD record
ord-936cda4a520241b19949ba0540926b42
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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