Water → HCID 20332408, compound

HRID 2057468Notes

Reaction equation

HRID 2057468 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][NH:5][C:4]2[C:13](=[O:21])[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:3]1=2.CI.[C:24](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:1]=[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]([CH3:24])[C:4]2[C:13](=[O:21])[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:3]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12377591HCID 12377591, compound

Product 1

HCID 20332408HCID 20332408, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 1,5-dihydro-1,5-dioxo-4H-1-benzopyrano[3,4-b]-pyridine-2-carboxylate (11.0 g, 0.0386 mole), methyl iodide (22.0 g, 0.154 mole) and potassium carbonate (10.7 g, 0.077 mole) in dimethylformamide (175 ml) is heated at 80° C. for 3 hours under nitrogen. The reaction mixture is cooled and poured into excess cold water. The product, which precipitated, is filtered off and recrystallized from dimethylformamide as white crystals (7.2 g, 62%), m.p. 203°-208° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe product, which precipitated
  3. filtrationis filtered off
  4. customrecrystallized from dimethylformamide as white crystals (7.2 g, 62%), m.p. 203°-208° C.

Sources & evidence

ORD record
ord-7236e3554684476d91b6d0cf20a714c6
Source dataset
uspto-grants-1980_07
Patent number
US04210758

Reaction notes

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