Sodium Carbonate → 7-(4-Acetylphenyl)-3-hydroxynaphthalene-2-carboxylic Acid

HRID 1361008Notes

Reaction equation

HRID 1361008 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:15])[C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:16]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)(=[O:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:16]([C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([OH:15])[C:8]([C:12]([OH:14])=[O:13])=[CH:9]3)=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)(=[O:18])[CH3:17]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 745032-Naphthalenecarboxylic acid, 7-bromo-3-hydroxy-HCID 37021224-Acetylphenylboronic acid

Product 1

HCID 574570427-(4-Acetylphenyl)-3-hydroxynaphthalene-2-carboxylic AcidYield 81.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

To 7-bromo-3-hydroxynaphthalene-2-carboxylic acid (100 mg, 0.37 mmol) (example 340) was added a solution of 4-acetylphenylboronic acid (92 mg, 0.56 mmol) in acetone (2.2 mL) followed by a solution of sodium carbonate (198 mg, 1.87 mmol) in water (3.3 mL). A suspension of palladium(II) acetate (4 mg, 0.02 mmol) in acetone (0.5 mL) was filtered and added to the above solution. The mixture was purged with N2 and stirred vigorously for 24 hours at room temperature. The reaction mixture was poured into 1 N hydrochloric acid (aq.) (60 mL) and the precipitate was filtered off and rinsed with water (3×40 mL). The crude product was dissolved in acetone (25 mL) and dried with magnesium sulfate (1 h). Filtration followed by concentration furnished the title compound as a solid (92 mg). 1H-NMR (DMSO-d6): δ 12.60 (1H, bs), 8.64 (1H, s), 8.42 (1H, s), 8.08 (2H, d), 7.97 (2H, d), 7.92 (2H, m), 7.33 (1H, s), 2.63 (3H, s); HPLC-MS (Method (A): m/z: 307 (M+1); Rt=3.84 min.

Workup

  1. filtrationwas filtered
  2. additionadded to the above solution
  3. customThe mixture was purged with N2
  4. additionThe reaction mixture was poured into 1 N hydrochloric acid (aq.) (60 mL)
  5. filtrationthe precipitate was filtered off
  6. washrinsed with water (3×40 mL)
  7. dissolutionThe crude product was dissolved in acetone (25 mL)
  8. dry with materialdried with magnesium sulfate (1 h)
  9. filtrationFiltration
  10. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-cb16a0ff8bd14ee693e79a2700529384
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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