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

HRID 2107616Notes

Reaction equation

HRID 2107616 reaction equation
[CH3:1][C:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10](Cl)=[C:5]2[S:4][CH:3]=1.[NH2:17][C:18]1[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=1>C1(OC)C=CC=CC=1>[CH3:1][C:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])=[C:5]2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 23046143Ethyl 3-methyl-7-chlorothieno[3,2-b)pyridine-6-carboxylate

Product 1

HCID 23046138Ethyl 3-methyl-7-(2-methylphenylamino)thieno[3,2-b]-pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Ethyl 3-methyl-7-chlorothieno[3,2-b]pyridine-6-carboxylate (3.0 g, 0.0117 mol) and o-toluidine (2.51 g, 0.0234 mol) in anisole (30 ml) were heated under reflux for three hours. The solvent was evaporated under reduced pressure, taken up in chloroform and washed in turn with 2NHCl, H2O, aqNa2CO3, H2O and brine, dried and evaporated to give an oil. This oil was purified by flash chromatography (silica, 40-60 mesh) using dichloromethane as eluant to give a buff coloured solid. This was crystallised from methanol to give the title compound, 2.3 g, m.p. 132°-134°.

Workup

  1. temperatureunder reflux for three hours
  2. customThe solvent was evaporated under reduced pressure
  3. washwashed in turn with 2NHCl, H2O, aqNa2CO3, H2O and brine
  4. customdried
  5. customevaporated
  6. customto give an oil
  7. customThis oil was purified by flash chromatography (silica, 40-60 mesh)
  8. customto give a buff
  9. customThis was crystallised from methanol

Sources & evidence

ORD record
ord-bbf6de0c19bb4bee96ccb0f90aab53b8
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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