| Identification | Back Directory | [Name]
2-CHLORO-5,6,7,8-TETRAHYDRO-1,6-NAPHTHYRIDINE HYDROCHLORIDE | [CAS]
766545-20-4 | [Synonyms]
2-chloro-5
8-tetrahydro-1
6-naphthyridine hydrochloride
2-CHLORO-5,6,7,8-TETRAHYDRO-1,6-NAPHTHYRIDINE HCL
2-CHLORO-5,6,7,8-TETRAHYDRO-1,6-PHTHYRIDINE HYDROCHLORIDE
1,6-Naphthyridine, 2-chloro-5,6,7,8-tetrahydro-, hydrochloride | [Molecular Formula]
C8H10Cl2N2 | [MDL Number]
MFCD09835503 | [MOL File]
766545-20-4.mol | [Molecular Weight]
168.62 |
| Questions And Answer | Back Directory | [Uses]
1,6-Naphthidine is one of the most widely studied diazanaphthalene compounds. It is a heterocyclic system composed of two aromatic fused rings containing nitrogen heteroatoms, possessing a unique rigid planar structure that exhibits excellent photophysical and photochemical properties. Therefore, it has wide applications in organic light-emitting materials, optoelectronic devices, fluorescent chemical sensors, organic molecular catalysis, and coordination chemistry. With the deepening research on 1,6-naphthidine, derivatives formed by introducing various groups onto the 1,6-naphthidine ring can interact with small biological molecules or metal ions and possess controllable photophysical properties. In particular, some 1,6-naphthidine derivatives exhibit good physiological activity and have been clinically applied in the treatment of certain diseases. |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride from 6-benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine was as follows: 6-benzyl-2-chloro-7,8-dihydro-5H-1,6-diazanaphthalene (2.70 g, 10.43 mmol, 1.00 eq.) was dissolved in ethylene chloride (50.00 mL) in dichloroethane (50.00 mL) and 1-chloroethyl carbonyl chloride (2.24 g, 15.65 mmol, 1.50 eq.) was added. The reaction was carried out at 15 °C under nitrogen protection. The reaction mixture was warmed up to 85 °C and the reaction was stirred for 12 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure. Methanol (50.00 mL) was added to the residue, heated to 80 °C and stirred for 2 hours. The reaction mixture was cooled and filtered, the filter cake was collected and dried to afford 2-chloro-5,6,7,8-tetrahydro-1,6-diazanaphthalene hydrochloride (2.00 g, 9.75 mmol, 93.50% yield) as a white solid. The resulting product was used directly in the next reaction without further purification. | [References]
[1] Patent: EP3252059, 2017, A1. Location in patent: Paragraph 0118; 0335-0337
[2] Patent: CN106467537, 2017, A. Location in patent: Paragraph 0151; 0152; 0161; 0162
[3] Patent: CN106467538, 2017, A. Location in patent: Paragraph 0181; 0190; 0191 |
|
|