Phosphorus oxychloride → 4-Chloro-6-iodoquinoline-3-carbonitrile

반응식

[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]([C:12]#[N:13])[C:5]2=O.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=[CH:7][C:6]=1[C:12]#[N:13]

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 289765906-Iodo-4-oxo-1,4-dihydroquinoline-3-carbonitrile

생성물 1

HCID 224667694-Chloro-6-iodoquinoline-3-carbonitrile수율 98%

실험 절차

A mixture of 6 6-iodo-4-oxo-1,4-dihydro-quinoline-3-carbonitrile (example 14b) (100 g, 0.34 mol) in phosphorus oxychloride (300 mL) was refluxed under N2 for 7 h. After cooling, the solvent was removed by rotary evaporator and then by the oil pump. Sat. sodium bicarbonate (200 mL) and ice water were slowly added. The solid was collected by filtration, washed with sat. sodium bicarbonate, water and dried to obtain 4-chloro-6-iodo-quinoline-3-carbonitrile (58 g, 98%) as a yellow solid. LC-MS m/e 315 (MH+).

후처리

temperaturewas refluxed under N2 for 7 h
temperatureAfter cooling
customthe solvent was removed by rotary evaporator
additionSat. sodium bicarbonate (200 mL) and ice water were slowly added
filtrationThe solid was collected by filtration
washwashed with sat. sodium bicarbonate, water
customdried

출처 및 근거

ORD 기록: ord-2fda928f72ed4c278ade8f07219a366f
출처 데이터셋: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07250515B2

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