Methyl iodide → HCID 19843279, compound

HRID 2352537Notes

Reaction equation

HRID 2352537 reaction equation
[CH3:1][C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:8]=2[OH:11])[CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][N:5]([CH3:17])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469606HCID 178469606, compound

Product 1

HCID 19843279HCID 19843279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 2-methyl-7-hydroxythieno[3,2-b]pyridine-6-carboxylate (21 g), potassium carbonate (12.2 g) and dry dimethylformamide (750 ml) was stirred at ambient temperature and iodomethane (6 ml) added. The mixture was stirred at ambient temperature for approximately 3.5 hours, then at 60° for 2 hours. The solvent was removed under reduced pressure to give a residue which on treatment with water (300 ml) gave the novel compound ethyl 2,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate, m.p. 143°-144°.

Workup

  1. stirringThe mixture was stirred at ambient temperature for approximately 3.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue which on treatment with water (300 ml)

Sources & evidence

ORD record
ord-c78e3de3e2fa4406a0348c0c45990bb1
Source dataset
uspto-grants-1989_10
Patent number
US04877793

Reaction notes

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