5-Bromonicotinamide → 5-Bromonicotinonitrile

반응식

P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([CH:15]=1)[C:12]([NH2:14])=O>>[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:12]#[N:14])[CH:15]=1

참가 물질

반응물 2

HCID 18085-Bromonicotinamide

HCID 24813Phosphorus oxychloride

생성물 1

HCID 7367935-Bromonicotinonitrile수율 82%

실험 절차

Phosphorus oxychloride (5 ml) was added to 5-bromonicotinamide (2 g, 10 mmol, Avocado Research Chemicals, Ltd.) and the mixture was heated to gentle reflux for 3 hours. The mixture was allowed to cool to room temperature, poured onto ice (100 g) and extracted with ethyl acetate (3×100 mL). The combined extracts were washed successively with aqueous ammonium hydroxide and water, dried (MgSO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by chromatography (SiO2, ethyl acetate:hexanes, 1:1) to provide the title compound (1.5 g, 82% yield). MS (DCI/NH3) m/z 184 (M+H)+.

후처리

temperaturethe mixture was heated
temperatureto gentle reflux for 3 hours
additionpoured onto ice (100 g)
extractionextracted with ethyl acetate (3×100 mL)
washThe combined extracts were washed successively with aqueous ammonium hydroxide and water
dry with materialdried (MgSO4)
filtrationfiltered
concentrationthe filtrate concentrated under reduced pressure
customThe residue was purified by chromatography (SiO2, ethyl acetate:hexanes, 1:1)

출처 및 근거

ORD 기록: ord-5ed26cd2492b48b394801e0e509cf8f4
출처 데이터셋: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06809105B2

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