Dimethyl Sulfate → Ethyl 4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

HRID 1280451Notes

Reaction equation

HRID 1280451 reaction equation
S(OC)(O[CH3:5])(=O)=O.[OH:8][C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11]2[CH:20]=[CH:21][S:22][C:10]=12.[OH-].[K+]>O>[CH3:5][N:12]1[CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9](=[O:8])[C:10]2[S:22][CH:21]=[CH:20][C:11]1=2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 178469639HCID 178469639, compound

Product 1

HCID 22250098Ethyl 4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Dimethyl sulphate (3.9 ml) can be added to a stirred solution of ethyl 7-hydroxythieno[3,2-b]-pyridine-6-carboxylate (4.63 g) and potassium hydroxide (3.5 g) in water (50 ml) at 0° C.-5° C. More water (20 ml) can be added and the mixture can be stirred at ambient temperature for 24 hours. The solid product can be collected by filtration, washed with water and dried to give the compound ethyl 4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate, m.p. 122° C.-128° C.

Workup

  1. filtrationThe solid product can be collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-f4937eb3c576454f8b5faada7179cf46
Source dataset
uspto-grants-2002_09
Patent number
US06451813B1

Reaction notes

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