Sodium Hydroxide → 2-(6,7-Dimethoxy-3,4-dihydronaphthalene-2-carboxamido)benzoic acid

HRID 2175709Notes

Reaction equation

HRID 2175709 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([C:15]([NH:17][C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20]([O:22]C)=[O:21])=[O:16])[CH2:7][CH2:6]2.[OH-].[Na+]>CO.C1COCC1>[CH3:14][O:13][C:12]1[CH:11]=[C:10]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][CH2:7][C:8]([C:15]([NH:17][C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20]([OH:22])=[O:21])=[O:16])=[CH:9]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67087821Methyl 2-(6,7-dimethoxy-1,2-dihydronaphthalene-3-carboxamido)benzoate

Product 1

HCID 670877322-(6,7-Dimethoxy-3,4-dihydronaphthalene-2-carboxamido)benzoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxamido)benzoate (440 mg, 1.2 mmol) in MeOH (6 mL) and THF (3 mL) was added 2N NaOH (3 mL) dropwise at room temperature. The resulting solution was stirred at room temperature for 2 hours, then quenched with 1N HCl and diluted with water. The resulting suspension was filtered and the solid was dried under vacuum to give 2-(6,7-dimethoxy-1,2-dihydronaphthalene-3-carboxamido)benzoic acid (350 mg, 83%). 1H-NMR (400 MHz, DMSO-d6) δ 2.59 (t, J=8.4 Hz, 2H), 2.83 (t, J=8.4 Hz, 2H), 3.75 (s, 3H), 3.79 (s, 3H), 6.90 (s, 1H), 6.97 (s, 1H), 7.15 (app t, J=7.6 Hz, 1H), 7.39 (s, 1H), 7.62 (m, 1H), 8.03 (dd, J=8.0, 1.6 Hz, 1H), 8.69 (d, J=8.4 Hz, 1H), 11.89 (s, 1H); LC-MS (ES-API); rt 9.22 min; m/z calculated for C20H19NO5 [M+Na]+ 376.1, found 376.1.

Workup

  1. customquenched 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-63cee3aa9bdf409ab45d7cdfe72422bd
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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