Methanol → 2-Hydroxy-6-nitrobenzonitrile

HRID 711721노트

반응식

HRID 711721 반응식
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+]([O-])=O)[C:5]=1[C:6]#[N:7])([O-:3])=[O:2].Cl.N1C=CC=CC=1.C[OH:23]>>[OH:23][C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[C:6]#[N:7]

참가 물질

4

반응물 3

HCID 887Methanol2회HCID 520718DinitrobenzonitrileHCID 10176127Pyridinium chloride

생성물 1

HCID 125032052-Hydroxy-6-nitrobenzonitrile수율 87%

실험 절차

To a solution of 2,6-dinitrobenzonitrile (10.0 g, 52.3 mmol) in MeOH (215 mL), was added a solution of Na (1.32 g, 57.5 mmol) in MeOH (23.3 mL). The reaction was refluxed under N2 for 2.5 hours, cooled to rt and the precipitate was collected by filtration. The resulting residue was combined with pyridine hydrochloride (15.1 g, 130 mmol), and the solids were melted at 200° C. for 18 hours. Upon completion, the reaction was cooled to rt, washed with brine (1×300 mL) and extracted with EtOAc (2×500 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated to provide 2-hydroxy-6-nitrobenzonitrile (6.70 g, 87%). 1H NMR (400 MHz, MeOD) δ 7.35 (dd, J=8.3, 0.8 Hz, 1H), 7.67 (t, J=8.2 Hz, 1H), 7.77 (dd, J=8.2, 1.1 Hz, 1H).

후처리

  1. temperatureThe reaction was refluxed under N2 for 2.5 hours
  2. filtrationthe precipitate was collected by filtration
  3. customfor 18 hours
  4. temperatureUpon completion, the reaction was cooled to rt
  5. washwashed with brine (1×300 mL)
  6. extractionextracted with EtOAc (2×500 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7ca744a0b1ae4b33abb43d15f8d0c5ec
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181276B2

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