Sodium Hydroxide → 7-Nitrobenzo[b]thiophene-2-carboxylic acid

HRID 1986641Notes

Reaction equation

HRID 1986641 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>C1COCC1.CO>[N+:14]([C:10]1[C:8]2[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH:13]=[CH:12][CH:11]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57722418Methyl 7-nitrobenzo[b]thiophene-2-carboxylate

Product 1

HCID 131624097-Nitrobenzo[b]thiophene-2-carboxylic acidYield 98.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a suspension of 7-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (1.0 g) in THF/MeOH (40 mL/40 mL) was added 8.4 mL (2.0 eq) of 1N NaOH. The reaction was stirred at room temperature for 2 h. The solvent was removed in vacuo. The residue was diluted with H2O/EtOAc, acidified with 3N HCl and extracted with EtOAc. The organics were dried over MgSO4, filtered and concentrated to give 7-nitro-benzo[b]thiophene-2-carboxylic acid as a light yellow solid (928 mg, 98% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was diluted with H2O/EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-84f3ef4ee5d24f729134fefc3c7087cc
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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