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| | 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one Basic information |
| Product Name: | 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one | | Synonyms: | 8-CHLORO-5,6-DIHYDRO-11H-BENZO-(5,6)-CYCLOHEPTA-(1,2-B)-PYRIMIDINE-11-ON;8-Chloro-10,11-dihydro-4-aza-5;8-chloro-10,11-dihydro-4-AZA-5H-benzo〔A,D〕cyclohepta-5-one;8-CHLORO-5,6-DIHYDRO-11H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIMIDINE-11-ONE;4-Aza-8-chloro-10,11-dihydro-5H-benzo[a,d]cyclo-5-heptanone;8-CHLORO-10,11-DIHYDRO-4 AZA-5H-BENZO[A,D] CYCLOHEPTAN-5-ONE =98%;8-CHLORO-5,6-DIHYDRO-11H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN-11-ONE;8-CHLORO-10,11-DIHYDRO-4-AZA-5H-DIBENZO-(A,D)CYCLOHEPTAN-5-ONE | | CAS: | 31251-41-9 | | MF: | C14H10ClNO | | MW: | 243.69 | | EINECS: | 700-257-5 | | Product Categories: | Aromatics Compounds;Intermediates;Heterocycles;Aromatics | | Mol File: | 31251-41-9.mol | ![8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one Structure](CAS/GIF/31251-41-9.gif) |
| | 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one Chemical Properties |
| Melting point | 90-92°C | | Boiling point | 433.6±45.0 °C(Predicted) | | density | 1.313±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 3.14±0.20(Predicted) | | form | Solid | | color | Pale Yellow to Pale Brown | | Major Application | pharmaceutical | | InChI | InChI=1S/C14H10ClNO/c15-11-5-6-12-10(8-11)4-3-9-2-1-7-16-13(9)14(12)17/h1-2,5-8H,3-4H2 | | InChIKey | WMQNOYVVLMIZDV-UHFFFAOYSA-N | | SMILES | C12C(=O)C3=CC=C(Cl)C=C3CCC1=CC=CN=2 | | CAS DataBase Reference | 31251-41-9(CAS DataBase Reference) |
| Hazard Codes | Xi | | WGK Germany | WGK 3 | | HS Code | 2933997500 | | Storage Class | 11 - Combustible Solids |
| | 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one Usage And Synthesis |
| Chemical Properties | Yellow Solid | | Uses | 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (Loratadine EP Impurity B; Loratadine USP Related Compound C) is a Loratadine intermediate. Loratidine impurity C. | | Synthesis | General procedure for the synthesis of 8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one from 3-(3-chlorophenylethyl)pyridine-2-carbonitrile: 8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (10 g) obtained in step C was dissolved in trifluorosulfonic acid (80 ml) and the reaction was stirred at 60 °C for 1 hour. Subsequently, aqueous 6N hydrochloric acid (80 ml) was added slowly and dropwise at room temperature. The reaction mixture was refluxed for 1 hour and poured into ice water. The reaction solution was neutralized with 50% aqueous sodium hydroxide, the precipitate precipitated was separated, washed with water and recrystallized by solvent mixture of isopropanol/water (3:1) to afford the target product 8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one. The mother liquor was concentrated and the residue was washed sequentially with water and chloroform to afford additionally 8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (9.4 g, yield 94%).1H NMR (MeOD-d4) δ: 3.3-3.4 (m, 2H), 3.4-3.5 (m, 2H), 7.5 (m, 2H), 8.1-8.2 (m, 2H), 8.7 (d, 1H), 8.9 (d, 1H). | | References | [1] Patent: WO2006/116157, 2006, A2. Location in patent: Page/Page column 56-57
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 6, p. 1778 - 1782
[3] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 457 - 461 |
| | 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one Preparation Products And Raw materials |
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