Thionyl Chloride → 3-Hydroxynaphthalene-2-carbonitrile

반응식

C([O:4][C:5]1[C:6]([C:15]([NH2:17])=O)=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(=O)C.S(Cl)(Cl)=O>>[OH:4][C:5]1[C:6]([C:15]#[N:17])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

참가 물질

반응물 2

HCID 24386Thionyl Chloride

HCID 18936915HCID 18936915, 화합물

생성물 1

HCID 129902643-Hydroxynaphthalene-2-carbonitrile수율 66%

실험 절차

A mixture of 19 (4.96 g, 21.6 mmol) and thionyl chloride (6.32 ml, 86.4 mmol) was heated under reflux for 2 hours. The solution was concentrated in vacuo to dryness. The residue was taken up in water (10 ml), methanol (200 ml) and 1N NaOH solution (75 ml). The solution was stirred at room temperature for 19 hours and concentrated. Chromatography, eluting with 1:1 cyclohexane/ethyl acetate, provided 2.41 g (66%) of 20 as yellow crystals, mp 188°-189° C. (lit. mp 188°-189° C.).

후처리

temperaturewas heated
temperatureunder reflux for 2 hours
concentrationThe solution was concentrated in vacuo to dryness
concentrationconcentrated
washChromatography, eluting with 1:1 cyclohexane/ethyl acetate

출처 및 근거

ORD 기록: ord-0dbeaabbd07e42f8b58841d4fed27806
출처 데이터셋: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05840739

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