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

HRID 2352535Notes

Reaction equation

HRID 2352535 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) was 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°-5°. More water (20 ml) was added and the mixture was stirred at ambient temperature for 24 hours. The solid product was collected by filtration, washed with water and dried to give the novel compound ethyl 4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate, m.p. 122°-128°.

Workup

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

Sources & evidence

ORD record
ord-64cf8c7b7c7f4cf4b4bb36f07678b950
Source dataset
uspto-grants-1989_10
Patent number
US04877793

Reaction notes

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