Hydrochloric Acid → Methyl 6-aminonaphthalene-1-carboxylate

HRID 2115844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2115844
FC(F)(F)S(O[C:7]1[CH:16]=C[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1C([O-])=O)(=O)=O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(=[NH:68])(C1C=CC=CC=1)C1C=CC=CC=1.Cl.[OH-].[Na+].C[CH2:73][O:74][C:75]([CH3:77])=[O:76]>C(COC)OC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:73][O:74][C:75]([C:77]1[C:14]2[C:9](=[CH:10][C:11]([NH2:68])=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:16]=1)=[O:76]

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 136809Benzophenone imineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 86608623HCID 86608623, Verbindung

Produkt 1

HCID 24823732Methyl 6-aminonaphthalene-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of methyl-6-(trifluoromethylsulfonyloxy-1-napthoate (2.0 g, 6.0 mmol) in dimethoxyethane (10 mL) was added Pd2(dba)3 (55 mg, 0.06 mmol), 2-(dicyclohexylphosphino)biphenyl (84 mg, 0.23 mmol), K3PO4 (1.9 g, 8.9 mmol) and benzophenone imine (1.25 mL, 7.5 mmol). The mixture was heated at 90° C. for 10 h. After cooling to ambient temperature, 2N HCl (4 mL) was added the mixture was stirred vigorously for 1 h. EtOAc (5 mL) was added to the reaction and the mixture was basified to pH 14 with 6N NaOH. The aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting brown residue was purified by silica gel column chromatography (0-25% EtOAc in hexanes) to give the title compound as a orange oil. MS (ESI, pos. ion) m/z: 202.1 (M+1). Mass Calc'd for C12H11NO2: 201.22.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. extractionThe aqueous layer was extracted with EtOAc (3×30 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting brown residue was purified by silica gel column chromatography (0-25% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-60b9bf42df324afb9c3a945f621e6424
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435823B2

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