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)

form 

Solid

pka

3.14±0.20(Predicted)

color 

Pale Yellow to Pale Brown

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)

Safety Information

Hazard Codes 

Xi

HS Code 

2933997500

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(31251-41-9)Related Product Information

• Pyridine hydrobromide
• Copper Pyrithione
• 2-Chloro-3-cyanopyridine
• Zinc pyrithione
• Benzo[b]thien-2-ylboronic acid
• Clopidol
• Pentachloropyridine
• Pyridine hydrofluoride
• 3-[2-(3-Chlorophenyl)ethyl]-2-pyridinecarbonitrile
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 4,8-Dichloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-β]pyridin-11-one (Loratadine Impurity)
• Loratadine Impurity 17
• 3-Hydroxy loratadine
• Loratadine Impurity 13
• Loratadine Impurity 13
• 8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol
• Loratadine Impurity 15
• Loratadine EP IMpurity F