4-Amino-m-cresol → Ethyl 3-methoxy-7-(4-hydroxy-2-methylphenylamino)thieno-[3,2-b]pyridine-6-carboxylate hydrochloride

HRID 2107625Notes

Reaction equation

HRID 2107625 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:12])=[C:6]2[S:5][CH:4]=1.[OH:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([CH3:26])[CH:20]=1>C1(OC)C=CC=CC=1>[ClH:12].[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:23][C:22]3[CH:24]=[CH:25][C:19]([OH:18])=[CH:20][C:21]=3[CH3:26])=[C:6]2[S:5][CH:4]=1

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 23046152Ethyl 3-methoxy-7-chlorothieno[3,2-b]pyridine-6-carboxylate

Product 1

HCID 23046154Ethyl 3-methoxy-7-(4-hydroxy-2-methylphenylamino)thieno-[3,2-b]pyridine-6-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Ethyl 3-methoxy-7-chlorothieno[3,2-b]pyridine-6-carboxylate (1.5 g, 0.0055 mol) and 4-hydroxy-2-methylaniline (1.36 g, 0.011 mol) in anisole (30 ml) were heated under reflux in an inert atmosphere for thirty hours. The solid obtained on cooling was collected by filtration and recrystallised from ethanol to give a brown crystalline solid, 1.09 g. Recrystallisation from ethanol after filtration through charcoal gave the title compound, 0.63 g, m.p. 286°-288°.

Workup

  1. temperatureunder reflux in an inert atmosphere for thirty hours
  2. customThe solid obtained
  3. temperatureon cooling
  4. filtrationwas collected by filtration
  5. customrecrystallised from ethanol
  6. customto give a brown crystalline solid, 1.09 g
  7. customRecrystallisation from ethanol
  8. filtrationafter filtration through charcoal

Sources & evidence

ORD record
ord-f8d7e40227da4da3ade15a2ccaae83af
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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