Hydrochloric Acid → 2-Methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-benzoic acid

HRID 2384887Notes

Reaction equation

HRID 2384887 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13]3[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[S:18][C:12]=3[C:11]2=[O:27])=[CH:6][C:5]=1[O:28][CH3:29].O.[OH-].[Li+].Cl>O1CCOCC1.O>[CH3:29][O:28][C:5]1[CH:6]=[C:7]([N:10]2[CH2:15][CH2:14][C:13]3[CH:16]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=4)[S:18][C:12]=3[C:11]2=[O:27])[CH:8]=[CH:9][C:4]=1[C:3]([OH:30])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 689510982-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-benzoic acid methyl ester

Product 1

HCID 689501452-Methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Dissolve 2-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-benzoic acid methyl ester (0.2274 g, 0.54 mmol) in dioxane (10 mL) and add lithium hydroxide monohydrate (124 mg, 2.69 mmol) followed by water (5 mL). Stir the reaction at RT overnight, dilute with water (10 mL), and acidify with 1 N HCl. Collect the solid by filtration and wash with water (2×10 mL) and Et2O (2×10 mL). Dry the solid in a vacuum oven to give 0.145 g (66%). LC-MS/ES m/z 410.3 [M+H]+.

Workup

  1. customthe reaction at RT overnight
  2. customCollect the solid
  3. filtrationby filtration
  4. washwash with water (2×10 mL) and Et2O (2×10 mL)
  5. customDry the solid in a vacuum oven
  6. customto give 0.145 g (66%)

Sources & evidence

ORD record
ord-08c6d556065747f3b945b4e5b7f5d232
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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