Hydrochloric Acid → Ethyl 3-(quinolin-2ylmethyl)-4-oxo-phthalazin-1-ylacetate

HRID 2165071Notes

Reaction equation

HRID 2165071 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][N:7]=1)[CH3:2].[H-].[Na+].Br[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.Cl>CN(C)C=O>[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[CH2:21][N:8]1[C:9](=[O:16])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:17])=[N:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 348622Ethyl 2-(4-oxo-3,4-dihydrophthalazin-1-yl)acetateHCID 124174182-(Bromomethyl)quinoline

Product 1

HCID 23043705Ethyl 3-(quinolin-2ylmethyl)-4-oxo-phthalazin-1-ylacetateYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl-4-oxo-3H-phthalazin-1-ylacetate (1.0 g) and sodium hydride (60% w/w dispersion in mineral oil) in dimethylformamide (30 ml) was added 2-bromomethylquinoline (1.05 g). The resulting solution was stirred at room temperature for 30 minutes, poured onto water (100 ml) containing 1N HCl (5 ml), and extracted with ethyl acetate. The organic extract was washed with water (3×50 ml), dried and evaporated to obtain ethyl 3-(quinolin-2ylmethyl)-4-oxo-phthalazin-1-ylacetate (1.54 g). This substance was dissolved in a water/dioxane mixture (70 ml/70 ml). To the solution was added 5N potassium hydroxide (5 ml). The solution was allowed to stir at room temperature for 15 minutes, concentrated to remove excess dioxane, diluted with water (150 ml) and extracted with ethyl acetate (3×70 ml). The aqueous layer was adjusted to pH 2 with concentrated HCl. The precipitated solid was triturated with hot ethyl acetate and then filtered to obtain the title compound (0.54 g; m.p. 193°-194° C.).

Workup

  1. additionpoured onto water (100 ml)
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water (3×50 ml)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-371f695395434b45829214d114bef0a8
Source dataset
uspto-grants-1990_07
Patent number
US04939140

Reaction notes

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