Hydrochloric Acid → Methyl 6-aminonaphthalene-1-carboxylate

HRID 1925346노트

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HRID 1925346 반응식
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]

참가 물질

10

반응물 7

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

생성물 1

HCID 24823732Methyl 6-aminonaphthalene-1-carboxylate

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7c5c70d2431c429ab684e8e3887f16b1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178557B2

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