Sodium Hydroxide → 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoic acid

HRID 2175696Notes

Reaction equation

HRID 2175696 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][C:7]([C:14]([NH:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20])=[O:15])=[CH:6]2.[OH-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][C:7]([C:14]([NH:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([OH:21])=[O:20])=[O:15])=[CH:6]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67087723methyl 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoate

Product 1

HCID 670877572-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoate (120 mg, 0.34 mmol) in THF (6 mL) and MeOH (3 mL) was added 2 N NaOH solution (0.85 mL) dropwise. The resulting mixture was stirred at room temperature for 2 h, then quenched with 1N HCl solution and extracted with DCM. The organic extracts were washed with a saturated aqueous NaCl solution and dried over sodium sulfate. The solvent was then removed under reduced pressure to give 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoic acid (100 mg, 87%). 1H-NMR (400 MHz, DMSO-d6) δ 3.72 (br s, 2H), 3.79 (s, 3H), 3.81 (s, 3H), 7.15 (m, 1H), 7.24 (s, 1H), 7.26 (s, 1H), 7.55-7.66 (m, 2H), 8.04 (dd, J=8.0, 1.6 Hz, 1H), 8.70 (dd, J=8.4, 1.2 Hz, 1H), 11.91 (s, 1H); LC-MS (ES-API); rt 9.23 min; m/z calculated for C19H17NO5 [M−H]− 338.1, found 338.1.

Workup

  1. customquenched with 1N HCl solution
  2. extractionextracted with DCM
  3. washThe organic extracts were washed with a saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-f9a4d3bb1a1c4a6eab20ffc5057c3516
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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