O-Toluidine → Ethyl 3-methoxy-7-(2-methylphenylamino)thieno-[3.2-b]pyridine-6-carboxylate

HRID 2107624Notes

Reaction equation

HRID 2107624 reaction equation
[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)=[C:6]2[S:5][CH:4]=1.[NH2:18][C:19]1[C:20]([CH3:25])=[CH:21][CH:22]=[CH:23][CH:24]=1>C1(OC)C=CC=CC=1>[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]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])=[C:6]2[S:5][CH:4]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 23046152Ethyl 3-methoxy-7-chlorothieno[3,2-b]pyridine-6-carboxylate

Product 1

HCID 23046156Ethyl 3-methoxy-7-(2-methylphenylamino)thieno-[3.2-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Ethyl 3-methoxy-7-chlorothieno[3,2-b]pyridin-6-carboxylate (1.5 g, 0.0055 mol) and o-toluidine (1.18 g, 0.011 mol) in anisole (30 ml) were heated under reflux in an inert atmosphere for twenty hours. The solvent was evaporated under reduced pressure and the residue was taken up in chloroform (200 ml) and washed with 2N hydrochloric acid (3×100 ml). The organic phase was then washed with sodium bicarbonate solution (2×100 ml), and water, dried over magnesium sulphate, filtered and evaporated to give an oil. The oil was purified by flash chromatography using dichloromethane as eluant. The fractions containing the product were combined and evaporated to give a colourless product, 1.12 g. Recrystallisation from ethyl acetate gave the title compound, 0.63 g, m.p. 141°-143°.

Workup

  1. temperatureunder reflux in an inert atmosphere for twenty hours
  2. customThe solvent was evaporated under reduced pressure
  3. washwashed with 2N hydrochloric acid (3×100 ml)
  4. washThe organic phase was then washed with sodium bicarbonate solution (2×100 ml), and water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil
  9. customThe oil was purified by flash chromatography
  10. additionThe fractions containing the product
  11. customevaporated
  12. customto give a colourless product, 1.12 g
  13. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-eee343bcca8f4218ad10514204af6f69
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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