Hydrochloric Acid → Methyl 6-aminonaphthalene-1-carboxylate

HRID 1925346ノート

反応式

HRID 1925346 の反応式
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]

参加物

10

反応物 7

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

生成物 1

HCID 24823732Methyl 6-aminonaphthalene-1-carboxylate

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7c5c70d2431c429ab684e8e3887f16b1
出典データセット
uspto-grants-2012_05
特許番号
US08178557B2

反応ノート

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