Sodium Hydroxide → 3-(1-Isopropylphthalazin-6-yl)-4-methylbenzoic acid

HRID 2357543Notes

Reaction equation

HRID 2357543 reaction equation
[CH:1]([C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:17]([O:19]CC)=[O:18])=[CH:11][CH:12]=2)[CH:7]=[N:6][N:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1.CO>[CH:1]([C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:17]([OH:19])=[O:18])=[CH:11][CH:12]=2)[CH:7]=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68455777Ethyl 3-(1-isopropylphthalazin-6-yl)-4-methylbenzoate

Product 1

HCID 684522933-(1-Isopropylphthalazin-6-yl)-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-(1-isopropylphthalazin-6-yl)-4-methylbenzoate (37.5 mg, 0.11 mmol) in tetrahydrofuran (0.3 mL) and methanol (0.15 mL) was treated with 1N aq. sodium hydroxide (0.28 mL, 0.28 mmol) and stirred at RT for 18 h. The reaction mixture was concentrated in vacuo and the residue was taken up in water. The pH was adjusted with 10% HCl solution to ˜7. The precipitate formed was collected via filtration and dried under high vacuum to afford the title compound as a maize-colored solid. MS (ES+): 307.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe precipitate formed
  3. filtrationwas collected via filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-a7e68c960a7c40c980802abcf80c3f6b
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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