Potassium Hydroxide → 3-(5-Bromobenzothiazole-2-ylmethyl)-4-oxo-3H-phthalazin-1-ylacetic acid

HRID 2165066Notes

Reaction equation

HRID 2165066 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([CH2:22][C:23]([O:25]CC)=[O:24])=[N:12]3)=[N:7][C:6]=2[CH:28]=1.O1CCOCC1.[OH-].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([CH2:22][C:23]([OH:25])=[O:24])=[N:12]3)=[N:7][C:6]=2[CH:28]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 14810636HCID 14810636, compound

Product 1

HCID 148106373-(5-Bromobenzothiazole-2-ylmethyl)-4-oxo-3H-phthalazin-1-ylacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-(5-bromobenzothiazol-2yl- methyl)-4-oxo-3-H-phthalazin-1-ylacetate (15.0 g) and dioxane (150 ml) was brought to solution by warming on a steam bath and to this solution was added a solution of 10% potassium hydroxide (20 ml) in ethanol (50 ml.). The resulting dark purple solution was stirred at room temperature for 2 hours and concentrated to remove excess dioxane and ethanol. The concentrate was diluted with water (100 ml) and the resulting solution was washed with ether (2×100 ml). The aqueous layer was collected and acidified to pH 2.0 by addition of concentrated HCl. The precipitated solid was crystallized from methylene chloride/ethanol (400 ml/40 ml) to obtain the product (Yield 7.65 g; m.p. 214° C.).

Workup

  1. temperatureby warming on a steam bath and to this solution
  2. concentrationconcentrated
  3. customto remove excess dioxane and ethanol
  4. additionThe concentrate was diluted with water (100 ml)
  5. washthe resulting solution was washed with ether (2×100 ml)
  6. customThe aqueous layer was collected
  7. additionacidified to pH 2.0 by addition of concentrated HCl
  8. customThe precipitated solid was crystallized from methylene chloride/ethanol (400 ml/40 ml)
  9. customto obtain the product (Yield 7.65 g; m.p. 214° C.)

Sources & evidence

ORD record
ord-62fa32788791448081c80efd505620b2
Source dataset
uspto-grants-1990_07
Patent number
US04939140

Reaction notes

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