Hydrochloric Acid → 3-Hydroxy-2-nitrobenzoic acid

HRID 921259

反応式

HRID 921259 の反応式
Cl[C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[K+].Cl.C(O)(C(F)(F)F)=[O:18]>O.O.CO>[OH:18][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 209023-Chloro-2-nitrobenzoic acid

生成物 1

HCID 2932913-Hydroxy-2-nitrobenzoic acid収率 66%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 22242641Methanol--water (1/1)溶媒

実験手順

To a 250 mL flask were added 3-chloro-2-nitrobenzoic acid (10 g, 49.6 mmol) and a potassium hydroxide solution (40 g, 727 mmol) in water (70 mL). The thick slurry was heated to reflux for 12 hours. The solution was cooled in ice and cautiously brought to pH 3 with concentrated HCl. The aqueous mixture was extracted with EtOAc (3×). The organic layers were combined, washed with brine, dried with sodium sulfate and concentrated in vacuo. The crude product mixture was dissolved in dichloromethane and the resulting yellow precipitate was filtered to afford Intermediate A-15A (6 g, 32.8 mmol, 66.0% yield). HPLC: RT=0.85 min (H2O/MeOH with TFA, Sunfire C18 3.5 μm, 2.1×30 mm, gradient=4 min, wavelength=220 nm); MS(ES): m/z=206 [M+Na]+; 1H NMR (400 MHz, chloroform-d) δ 7.56-7.35 (m, 1H), 7.23 (dd, J=7.9, 1.5 Hz, 1H).

後処理

  1. temperatureThe thick slurry was heated
  2. temperatureto reflux for 12 hours
  3. temperatureThe solution was cooled in ice
  4. extractionThe aqueous mixture was extracted with EtOAc (3×)
  5. washwashed with brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe crude product mixture was dissolved in dichloromethane
  9. filtrationthe resulting yellow precipitate was filtered
  10. customto afford Intermediate A-15A (6 g, 32.8 mmol, 66.0% yield)

出典と根拠

ORDレコード
ord-3861fac199d341acb9eafdea11cafeca
出典データセット
uspto-grants-2016_03
特許番号
US09273014B2

関連ノート

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