Phosphorus oxychloride → 2,6-Dichloroquinoline

반응식

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](O)[CH:6]=[CH:5]2.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 178515629HCID 178515629, 화합물

생성물 1

HCID 6075022,6-Dichloroquinoline수율 90%

실험 절차

180 mg 6-chloro-2-hydroxy quinoline was treated by 3 ml POCl3, the mixture was refluxed for 3 hours, the remaining POCl3 was evaporated out. After cooling to room temperature, the residue was treated by cold water, the solid was filtered out and dried as green powder, yield: 90%. Following the general procedure in claim 5, the listed compounds were achieved. Mass calculated for C9H5Cl2N: 198; LCMS: 200.1 (M+2)+; 1HNMR (400 MHZ), DMSO-d6) δ ppm 8.04 (1H, d, J=7.8 Hz), 7.97 (1H, d, J=8.8 Hz), 7.81 (1H, d, J=1.9 Hz), 7.68 (1H, dd, J=9.8 Hz, J=2.9 Hz), 7.42 (1H, d, J=8.8 Hz).

후처리

temperaturethe mixture was refluxed for 3 hours
customthe remaining POCl3 was evaporated out
additionthe residue was treated by cold water
filtrationthe solid was filtered out
customdried as green powder, yield: 90%

출처 및 근거

ORD 기록: ord-8ab2125dfc3e4565887e933bdb194c31
출처 데이터셋: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08455516B2

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