Hydrochloric Acid → 6-(4-Hydroxy-3-methoxy-phenyl)-2-(4-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

HRID 2384880Notes

Reaction equation

HRID 2384880 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][C:12]3[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[S:17][C:11]=3[C:10]2=[O:26])[CH:6]=[CH:5][C:4]=1[O:27]S(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+].CCO.Cl>O>[OH:27][C:4]1[CH:5]=[CH:6][C:7]([N:9]2[CH2:14][CH2:13][C:12]3[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[S:17][C:11]=3[C:10]2=[O:26])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 57649518Toluene-4-sulfonic acid 2-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-phenyl ester

Product 1

HCID 689509596-(4-Hydroxy-3-methoxy-phenyl)-2-(4-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-oneYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Combine toluene-4-sulfonic acid 2-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-phenyl ester (1.029 g, 1.92 mmol) and KOH (2.15 g, 38.48 mmol) with EtOH (30 mL) and water (20 mL). Reflux the reaction for 10 h and dilute with water (50 mL). Acidify with 5.0 M HCl (8 mL). Remove the organic solvent in vacuo and dilute the residue with water (10 mL). Collect the solid material by filtration and wash with water (3×10 mL) and Et2O (2×15 mL) then dry in a vacuum oven to give 0.646 g (88%) of the title compound. MS/ES m/z 382.0 [M+H]+.

Workup

  1. temperatureReflux
  2. customthe reaction for 10 h
  3. customRemove the organic solvent in vacuo
  4. additiondilute the residue with water (10 mL)
  5. customCollect the solid material
  6. filtrationby filtration
  7. washwash with water (3×10 mL) and Et2O (2×15 mL)
  8. customthen dry in a vacuum oven

Sources & evidence

ORD record
ord-e3bf5dfec2714364aead372e5df1478e
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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