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

HRID 1074552Notes

Reaction equation

HRID 1074552 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-863c636f839248dab2e21ca124183a41
Source dataset
uspto-grants-1983_07
Patent number
US04393062

Reaction notes

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