4-Methoxy-2-nitrobenzonitrile → 4-Hydroxy-2-nitrobenzonitrile

반응식

C[O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.Cl.N1C=CC=CC=1>>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1

참가 물질

반응물 2

HCID 2886654-Methoxy-2-nitrobenzonitrile

HCID 10176127Pyridinium chloride

생성물 1

HCID 534181214-Hydroxy-2-nitrobenzonitrile수율 26.5%

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온도: 200 °C

실험 절차

A mixture of 4-methoxy-2-nitrobenzonitrile (820 mg, 4.6 mmol) and pyridine hydrochloride (755 mg, 4.6 mmol) was heated at 200° C. under N2 for 18 hours. Upon completion, the reaction was cooled to room temperature, washed with brine and extracted with EtOAc (2×100 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (1:1 Hexane:EtOAc) to provide 4-hydroxy-2-nitrobenzonitrile (200 mg, 26%). 1H NMR (400 MHz, MeOD) δ 7.24 (dd, J=8.6, 2.4 Hz, 1H), 7.70 (d, J=2.4 Hz, 1H), 7.83 (d, J=8.6 Hz, 1H).

후처리

temperatureUpon completion, the reaction was cooled to room temperature
washwashed with brine
extractionextracted with EtOAc (2×100 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography (1:1 Hexane:EtOAc)

출처 및 근거

ORD 기록: ord-0d10c11930fd425b9418cb88afde6fe6
출처 데이터셋: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09181276B2

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