Sodium Hydroxide → HCID 14651986, compound

HRID 2175703Notes

Reaction equation

HRID 2175703 reaction equation
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[S:7][C:8]([C:10]([NH:12][C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[C:15]([O:17]C)=[O:16])=[O:11])=[CH:9][C:5]=2[CH:4]=1.[OH-].[Na+]>CO.C1COCC1>[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[S:7][C:8]([C:10]([NH:12][C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[C:15]([OH:17])=[O:16])=[O:11])=[CH:9][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67087747HCID 67087747, compound

Product 1

HCID 14651986HCID 14651986, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(5,6-dimethoxybenzo[b]thiophene-2-carboxamido)benzoate (650 mg, 1.75 mmol) in MeOH (9 mL) and THF (20 mL) was added 2N NaOH (9 mL) dropwise at room temperature. The resulting solution was stirred at room temperature for 2 hours. The reaction was quenched with 1N HCl and diluted with water. The resulting suspension was filtered and the solid was dried under vacuum to afford 2-(5,6-dimethoxybenzo[b]thiophene-2-carboxamido)benzoic acid (550 mg, 88%). LC-MS (ES-API); rt 9.22 min; m/z calculated for C18H15NO5S [M+Na]+ 380.1, found 380.0.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. additiondiluted with water
  3. filtrationThe resulting suspension was filtered
  4. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-7bba38a8022a4cfe81ab7cd62be037e9
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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