Sodium Hydroxide → Ethyl 3-methoxy-7-chlorothieno[3,2-b]pyridine-6-carboxylate

HRID 2107623Notes

Reaction equation

HRID 2107623 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[NH:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11](=O)[C:6]=2[S:5][CH:4]=1.[OH-].[Na+].P(Cl)(Cl)([Cl:22])=O>>[CH3:1][O:2][C:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([Cl:22])=[C:6]2[S:5][CH:4]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 230461573-Methoxy-6-ethoxycarbonylthieno[3,2-b]pyridin-7-(4H)-one

Product 1

HCID 23046152Ethyl 3-methoxy-7-chlorothieno[3,2-b]pyridine-6-carboxylate

Procedure

3-Methoxy-6-ethoxycarbonylthieno[3,2-b]pyridin-7-(4H)-one (3 g, 0.0118 mol) and phosphorus oxychloride (10 ml) was heated under reflux for one hour. The reaction mixture was poured onto ice (200 g) and stirred for 30 minutes. The mixture was then basified with 40% sodium hydroxide solution and extracted with chloroform (3×100 ml). The chloroform extracts were combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give the title compound as a buff-colour solid, 3.2 g, m.p. 135°-137°.

Workup

  1. temperatureunder reflux for one hour
  2. additionThe reaction mixture was poured onto ice (200 g)
  3. extractionextracted with chloroform (3×100 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ca478fce6eb344fbb1bc326c5c24ab94
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

Loading…