Sodium Hydroxide → 4-Methyl-3-(1-methylphthalazin-6-yl)benzoic acid

HRID 422550Notes

Reaction equation

HRID 422550 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([CH3:23])=[N:18][N:17]=[CH:16]2.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([CH3:23])=[N:18][N:17]=[CH:16]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59726018Ethyl 4-methyl-3-(1-methylphthalazin-6-yl)benzoate

Product 1

HCID 597260224-Methyl-3-(1-methylphthalazin-6-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-methyl-3-(1-methylphthalazin-6-yl)benzoate (51.7 mg, 169 μmol) in tetrahydrofuran (800 μl) and methanol (400 μl) was added 1N aqueous sodium hydroxide solution (338 μl, 338 μmol) and stirred at RT for 18 h. The reaction was concentrated in vacuo and the residue was taken up in water and the pH was adjusted with 10% aqueous HCl solution to ˜7. The aqueous mixture was extracted with 15% MeOH/CHCl3 (3×) and the organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo to give 4-methyl-3-(1-methylphthalazin-6-yl)benzoic acid as a maize solid. MS (ES+): 279.1 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionThe aqueous mixture was extracted with 15% MeOH/CHCl3 (3×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-183274199dd54dd581858722a2eb47e7
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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