4-Amino-m-cresol → 6-Butyryl-7-(4-hydroxy-2-methylphenylamino)-3-methoxythieno[3,2-b]pyridine

HRID 2107629

Reaction equation

HRID 2107629 reaction equation
[C:1]([C:6]1[C:7](Cl)=[C:8]2[S:14][CH:13]=[C:12]([O:15][CH3:16])[C:9]2=[N:10][CH:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[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>[C:1]([C:6]1[C:7]([NH:23][C:22]2[CH:24]=[CH:25][C:19]([OH:18])=[CH:20][C:21]=2[CH3:26])=[C:8]2[S:14][CH:13]=[C:12]([O:15][CH3:16])[C:9]2=[N:10][CH:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 230461496-Butyryl-7-chloro-3-methoxythieno[3,2-b]pyridine

Product 1

HCID 230461516-Butyryl-7-(4-hydroxy-2-methylphenylamino)-3-methoxythieno[3,2-b]pyridine

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

6-Butyryl-7-chloro-3-methoxythieno[3,2-b]pyridine (1.5 g, 0.0056 mol) and 4-hydroxy-2-methylaniline (1.37 g, 0.011 mol) in anisole (30 ml) were heated under reflux in a nitrogen atmosphere for 36 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between chloroform and sodium bicarbonate solution. The insoluble material was filtered off. The chloroform layer was washed with sodium bicarbonate solution (2×100 ml), dried over magnesium sulphate, filtered and evaporated to give a brown solid. The product was purified by flash chromatography using chloroform as eluant. The solid obtained was recrystallised from ethanol to give the title compound, 0.81 g, m.p. 255°-257°.

Workup

  1. temperatureunder reflux in a nitrogen atmosphere for 36 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between chloroform and sodium bicarbonate solution
  4. filtrationThe insoluble material was filtered off
  5. washThe chloroform layer was washed with sodium bicarbonate solution (2×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a brown solid
  10. customThe product was purified by flash chromatography
  11. customThe solid obtained
  12. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-fed3c7e5755a45e6b84c6a56ff579aae
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Linked notes

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