Chlorine monoxide → 1,7-Dichloro-3-methylisoquinoline

반응식

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[NH:8][C:9]2=O)=[CH:4][CH:3]=1.O(Cl)[Cl:15]>>[Cl:15][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[C:7]([CH3:13])[N:8]=1

참가 물질

반응물 2

HCID 24646Chlorine monoxide

HCID 230846567-Chloro-3-methyl-1(2H)-isoquinolinone

생성물 1

HCID 213880331,7-Dichloro-3-methylisoquinoline

실험 절차

A solution of 7-chloro-3-methyl-2H-isoquinoline-1-one (7.1 g, 36.7 mmol) in 100 mL of phosporous oxychloride is heated to 100° C. After 5 h, the solution is concentrated to dryness. The residue is dissolved in CH2Cl2. The solution is washed with H2O. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 3% EtOAc/hexanes to 5% EtOAc/hexanes. The title compound is obtained as a white solid (6.0 g, 28 mmol). 1H NMR (CDCl3, 300 MHz) δ8.23 (s, 1H), 7.68 (m, 1H), 7.63 (m, 1H), 7.40 (s, 1H), 2.64 (s, 3H).

후처리

concentrationthe solution is concentrated to dryness
dissolutionThe residue is dissolved in CH2Cl2
washThe solution is washed with H2O
dry with materialThe organic layer is dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product is purified by column chromatography
washeluting with a gradient of 3% EtOAc/hexanes to 5% EtOAc/hexanes

출처 및 근거

ORD 기록: ord-5c72f8ccd0dc46f3b7fa0f57a18a6278
출처 데이터셋: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07612075B2

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