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| | 7-Chloro-1-hydroxyisoquinoline Basic information |
| Product Name: | 7-Chloro-1-hydroxyisoquinoline | | Synonyms: | 7-Chloro-1(2H)-isoquinolinone;7-CHLORO-1(2H)-ISOQUINOLONE;7-Chloroisoquinolin-1-ol;7-chloro-2H-isoquinolin-1-one;1(2H)-Isoquinolinone, 7-chloro-;7-chloro-1,2-dihydroisoquinolin-1-one;7-Chloro-1-hydroxyisoquinoline | | CAS: | 24188-74-7 | | MF: | C9H6ClNO | | MW: | 179.6 | | EINECS: | | | Product Categories: | | | Mol File: | 24188-74-7.mol |  |
| | 7-Chloro-1-hydroxyisoquinoline Chemical Properties |
| Melting point | 245-247 °C(Solv: methanol (67-56-1)) | | Boiling point | 414.9±45.0 °C(Predicted) | | density | 1.339±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | pka | 11.99±0.20(Predicted) | | Appearance | Off-white to light yellow Solid | | InChI | InChI=1S/C9H6ClNO/c10-7-2-1-6-3-4-11-9(12)8(6)5-7/h1-5H,(H,11,12) | | InChIKey | YWUCOQGBXQHOJM-UHFFFAOYSA-N | | SMILES | C1(=O)C2=C(C=CC(Cl)=C2)C=CN1 |
| | 7-Chloro-1-hydroxyisoquinoline Usage And Synthesis |
| Uses | 7-Chloroisoquinolin-1(2H)-one acts as a reagent for the preparation, SAR of methoxyisoquinoline derivative and discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection. Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists. | | Synthesis | Step 1: Diphenyl phosphate azide (DPPA, 27.5 g, 0.1 mol) was added dropwise to a solution of (E)-3-(4-chlorophenyl)acrylic acid (18.3 g, 0.1 mol) and triethylamine (Et3N, 20.2 g, 0.2 mol) in benzene (100 mL). After stirring the reaction mixture for 2 h, the solution was concentrated and purified by fast chromatography (Biotage system, mobile phase 20/80 ethyl acetate/hexane) to give 16 g of the intermediate azide as a solid. The intermediate was dissolved in 100 mL of 1,2-dichloroethane and the resulting mixture was slowly heated to 90 °C over 30 min. The reaction mixture was then heated to reflux and held at this temperature for 3 hours. After cooling to room temperature, a solid was precipitated, collected by filtration and washed with toluene to give 9.5 g of 7-chloroisoquinolin-1(2H)-one in 53% yield.
Product characterization data.
1H NMR (400 MHz, CD3OD) δ ppm: 6.66 (d, J = 7.05 Hz, 1H), 7.18 (d, J = 7.05 Hz, 1H), 7.66 (s, 1H), 7.67 (d, J = 2.01 Hz, 1H), 8.24 (d, J = 2.27 Hz, 1H).
13C NMR (101 MHz, DMSO-D6) δ ppm: 104.05, 125.62, 127.21, 128.54, 129.52, 130.77, 132.43, 136.55, 160.72.
LC/MS, MS m/z (M + H)+: 180. | | References | [1] Patent: WO2012/166459, 2012, A1. Location in patent: Page/Page column 23-24 |
| | 7-Chloro-1-hydroxyisoquinoline Preparation Products And Raw materials |
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