Potassium Hydroxide → HCID 14810790, compound

HRID 2165068Notes

Reaction equation

HRID 2165068 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:21][C:22]([O:24]C)=[O:23])=[N:11]1.[OH-].[K+]>CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:21][C:22]([OH:24])=[O:23])=[N:11]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23043717HCID 23043717, compound

Product 1

HCID 14810790HCID 14810790, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-(2-benzothiazolyl)-4-oxo-3H-phthalazin-1-ylacetate (1.92 g) in methanol (50 ml) containing 10% aqueous potassium hydroxide (5 ml) was stirred at room temperature for 4 hours. The solution was concentrated to remove methanol and the concentrate was diluted with water (75 ml) and then extracted with ethyl acetate. The aqueous portion was separated and acidified with concentrated hydrochloric acid to pH 2.0. The precipitated solid was collected and crystallized from isopropyl alcohol to give 3-(2-benzothiazolyl)-4-oxo-3-H-phthalazin-1-ylacetic acid (876 mg; m.p. 205° C.(d)).

Workup

  1. concentrationThe solution was concentrated
  2. customto remove methanol
  3. additionthe concentrate was diluted with water (75 ml)
  4. extractionextracted with ethyl acetate
  5. customThe aqueous portion was separated
  6. customThe precipitated solid was collected
  7. customcrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-86429704d10b40fe981180083ebc313d
Source dataset
uspto-grants-1990_07
Patent number
US04939140

Reaction notes

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