Water → Methyl 3,4-dihydro-6-methoxy-4-oxo-1-phthalazinecarboxylate

HRID 1413797Notes

Reaction equation

HRID 1413797 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]([OH:16])=[O:15])=[N:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.[C:17](=O)([O-])O.[Na+].CI.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]([O:16][CH3:17])=[O:15])=[N:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 20495856HCID 20495856, compound

Product 1

HCID 20495817Methyl 3,4-dihydro-6-methoxy-4-oxo-1-phthalazinecarboxylateYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-methoxy-1,2-dihydro-1-oxophthalazin-4-ylcarboxylic acid (10.0 g.), sodium hydrogen carbonate (15.0 g.) and methyl iodide (15.0 ml.) in dry dimethylformamide (200 ml.) was stirred at room temperature for 16 hours. The mixture was then poured into water (600 ml.). The precipitated solid was separated, washed first with water then cold methanol, and then recrystallised from methanol to give methyl 7-methoxy-1,2-dihydro-1-oxophthalazin-4-ylcarboxylate (8.6 g.), m.p. 222°-225° C.

Workup

  1. customThe precipitated solid was separated
  2. washwashed first with water
  3. customcold methanol, and then recrystallised from methanol

Sources & evidence

ORD record
ord-2d3fa7b361a74b0ab375a9c0be2f81a9
Source dataset
uspto-grants-1981_02
Patent number
US04251528

Reaction notes

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