Hydrochloric Acid → 3-Hydroxy-2-nitrobenzoic acid

HRID 921259

반응식

HRID 921259 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 2932913-Hydroxy-2-nitrobenzoic acid수율 66%

시약·촉매·용매 2

HCID 962Water용매HCID 22242641Methanol--water (1/1)용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3861fac199d341acb9eafdea11cafeca
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273014B2

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