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ChemicalBook--->CAS DataBase List--->80947-25-7

80947-25-7

80947-25-7 Structure

80947-25-7 Structure
IdentificationBack Directory
[Name]

4-AMINO-2-CHLOROQUINOLINE
[CAS]

80947-25-7
[Synonyms]

2-Chloroquinolin-4-amine
2-Chloro-4-quinolinamine
4-Quinolinamine,2-chloro-
4-AMINO-2-CHLOROQUINOLINE
(2-Chloroquinolin-4-yl)amine
[Molecular Formula]

C9H7ClN2
[MDL Number]

MFCD08705643
[MOL File]

80947-25-7.mol
[Molecular Weight]

178.62
Chemical PropertiesBack Directory
[Melting point ]

250℃
[Boiling point ]

366℃
[density ]

1.363
[Fp ]

175℃
[storage temp. ]

under inert gas (nitrogen or Argon) at 2–8 °C
[pka]

4.24±0.50(Predicted)
[Appearance]

White to light brown Solid
[InChI]

InChI=1S/C9H7ClN2/c10-9-5-7(11)6-3-1-2-4-8(6)12-9/h1-5H,(H2,11,12)
[InChIKey]

QVCRGJALYOLXDC-UHFFFAOYSA-N
[SMILES]

N1C2C(=CC=CC=2)C(N)=CC=1Cl
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H302-H335
[Precautionary statements ]

P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501
[HS Code ]

2933499090
Spectrum DetailBack Directory
[Spectrum Detail]

4-AMINO-2-CHLOROQUINOLINE(80947-25-7)1HNMR
Hazard InformationBack Directory
[Synthesis]

2,4-DICHLOROQUINOLINE

703-61-7

4-AMINO-2-CHLOROQUINOLINE

80947-25-7

The general procedure for the synthesis of 4-amino-2-chloroquinoline from 2,4-dichloroquinoline is as follows: the synthesis of compound 9 has been reported in the literature [von Btichi, J. et al. Die Tuberkulostatische Wirkung von 2-Oxy-4-amino-chinolin Derivaten. Helv. Chim. Acta. 1949, 32, 1806-1814; Wojahn, H. Untersuchungen ber den Zusammenhang von chemischer Konstitution und anasthesierender Wirkung bei 2- Alkoxy-chinolin Derivaten. Arch. Pharm. 1936, 274, 83-106]. However, in the present experiments, compound 9 was prepared by the following method. the brief procedure was as follows: compound 8 (0.35 g, 1.8 mmol) was suspended in 28-30% aqueous ammonia solution (3 mL). The reaction was carried out in a microwave reactor at 160 °C for 2.5 hours. Upon completion of the reaction, the ammonia was removed by evaporation. The product was purified by column chromatography using dichloromethane solution containing 3% methanol as eluent. Yield: 0.14 g (44%).1H NMR (CDCl3) δ 4.83 (broad single peak, 2H, NH2), 6.62 (single peak, 1H, aromatics), 7.43-7.51 (multiple peaks, 1H, aromatics), 7.63-7.73 (multiple peaks, 2H, aromatics), 7.89-7.95 (multiple peaks, 1H, aromatics).13C NMR ( 600 MHz, CDCl3) δ 103.07, 117.60, 120.08, 125.27, 129.13, 130.46, 148.26, 151.40, 151.41.

[References]

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 4, p. 926 - 931
[2] Patent: WO2010/20981, 2010, A1. Location in patent: Page/Page column 30; 2/2
[3] Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 332, p. 72 - 86
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