Methyl iodide → HCID 21389231, compound

HRID 1833367Notes

Reaction equation

HRID 1833367 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:13]3[C:12](=[O:15])[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][NH:9][C:8]=3[C:7](=[O:21])[C:6]=2[CH:22]=1.CI.[C:25](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:25][N:9]1[CH:10]=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12](=[O:15])[C:13]2[O:14][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:22][C:6]=3[C:7](=[O:21])[C:8]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12736922HCID 12736922, compound

Product 1

HCID 21389231HCID 21389231, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 8-chloro-4,10-dihydro-4,10-dioxo-1H-1-benzopyrano[3,2-b]pyridine-3-carboxylate (0.5 g, 0.0016 mole), methyl iodide (0.5 g, 0.0035 mole) and potassium carbonate (0.23 g, 0.0017 mole) in dimethyl formamide (25 ml) was stirred at 100° for 3 hrs. under nitrogen. The reaction mixture was cooled. The product, which precipitated, was filtered, washed with water and dried. Recrystallization from DMF gave white crystals (0.47 g, 90%), m.p. 295°-297°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe product, which precipitated
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried
  6. customRecrystallization from DMF

Sources & evidence

ORD record
ord-54840fd7f9dd4ea4bc6ff89850bd823e
Source dataset
uspto-grants-1978_01
Patent number
US04066655

Reaction notes

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