2-(6,7-Dimethoxy-3,4-dihydronaphthalene-2-carboxamido)benzoic acid → 2-(6,7-Dimethoxy-1,2,3,4-tetrahydronaphthalene-3-carboxamido)benzoic acid

HRID 2175710Notes

Reaction equation

HRID 2175710 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:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])=[O:16])[CH2:7][CH2:6]2>CO.C1COCC1.[Pd]>[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][CH:8]([C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])=[O:16])[CH2:9]2

Participants

5

Reactant 1

HCID 670877322-(6,7-Dimethoxy-3,4-dihydronaphthalene-2-carboxamido)benzoic acid

Product 1

HCID 670877792-(6,7-Dimethoxy-1,2,3,4-tetrahydronaphthalene-3-carboxamido)benzoic acidYield 71%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxamido)benzoic acid (350 mg, 1 mmol) and 10% Pd/C (35 mg) in MeOH (50 mL) and THF (50 mL) was stirred at room temperature under H2 overnight. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford 2-(6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-3-carboxamido)benzoic acid (250 mg, 71%). 1H-NMR (400 MHz, DMSO-d6) δ 1.70-1.85 (m, 1H), 2.10-2.21 (m, 1H), 2.64-2.82 (m, 3H), 2.82-3.00 (m, 2H), 3.71 (s, 6H), 6.66 (s, 1H), 6.68 (s, 1H), 7.16 (app t, J=7.6 Hz, 1H), 7.60 (app t, J=8.0 Hz, 1H), 8.00 (d, J=7.2 Hz, 1H), 8.53 (d, J=8.4 Hz, 1H), 11.32 (s, 1H); LC-MS (ES-API); rt 8.96 min; m/z calculated for C20H21NO5 [M+H]+ 356.1, found 356.1.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f18075fc28c43848adad223ed18ccee
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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