Phosphorus oxychloride → 2-Chloro-6-methoxyquinoline

반응식

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8](O)[CH:7]=[CH:6]2.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 178488021HCID 178488021, 화합물

생성물 1

HCID 836472-Chloro-6-methoxyquinoline수율 86%

실험 절차

A solution of 6-methoxyquinolin-2-ol (400 mg, 2.29 mmol) in POCl3 (5.0 mL) was refluxed for 2 hours. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc (50 mL), the organic layer was washed with saturated NaHCO3 (30 mL×2), dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by silica gel column (PE/EtOAc=10/1) to give 2-chloro-6-methoxyquinoline (380 mg, yield 86%) as a solid. 1H NMR (CDCl3 400 MHz): δ 7.92 (d, J=8.4 Hz, 1H), 7.85 (d, J=9.2 Hz, 1H), 7.32-7.25 (m, 2H), 7.00 (d, J=2.4 Hz, 1H), 3.86 (s, 3H).

후처리

customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in EtOAc (50 mL)
washthe organic layer was washed with saturated NaHCO3 (30 mL×2)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give the crude product, which
customwas purified by silica gel column (PE/EtOAc=10/1)

출처 및 근거

ORD 기록: ord-907fec872cc948c49cc39345fa3751b3
출처 데이터셋: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09433618B2

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