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Home > Encyclopedia > 4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE

4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE

4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE structure
  • CAS No:

    214470-68-5

  • Formula:

    C14H12Cl2N2O2

  • Synonyms:

    4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE;4-Chloro-7-(3-chloropropoxy)-3-cyano-6-methoxyquinoline;4-Chloro-7-(3-chloropropoxy)-3-cyano-6-methyloxyquinoline;4-Chloro-7-(3-chloropropoxy)-6-methoxy-3-quinolinecarbonitrile;7-(3-chloro-propoxy)-4-chloro-6-Methoxy-quinoline-3-carbonitrile;3-Quinolinecarbonitrile, 4-chloro-7-(3-chloropropoxy)-6-Methoxy-

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

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Basic Attributes

  • 214470-68-5

  • C14H12Cl2N2O2

  • 311.16328

  • 310.027588

  • 55.1

  • 3.4

  • 1592732-453-0

  • BEGHZKYNLSIHIA-UHFFFAOYSA-N

  • 4

  • 0

  • 5

Characteristics

  • 1.37

  • 478.1°C at 760 mmHg

  • 243.0±27.3 °C

  • 1.608

Safety Information

Production Methods

A mixture of compound 25 (31.2 g, 0.10 mol), 2, 4-dichloro-5-methoxyaniline (30, 21.1 g, 0.11 mol), and pyridine hydrochloride (12.8 g, 0.11 mol) in 2-methoxyethanol (150 g) was heated to 120 C for 3 h. The suspension was cooled to r.t. and poured into water (600 g) while stirring. The resulting solid was filtered, washed with water (2 × 40 g), and dried at 50 C to give product 31 (35.9 g, 77%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): delta = 2.28 (m, J = 6.0 Hz, 2 H), 3.82 (t, J = 6.0 Hz, 2 H), 3.87 (s, 3 H), 3.97 (s, 3 H), 4.30 (t, J = 6.0 Hz, 2 H), 7.35(s, 1 H), 7.37 (s, 1 H), 7.75 (s, 1 H), 7.85 (s, 1 H), 8.43 (s, 1 H), 9.63 (s, 1H).13C NMR (100 MHz, DMSO-d6): delta = 31.9, 42.1, 56.7, 57.3, 65.8, 86.9, 102.4, 110.0, 113.1, 114.0, 117.4, 120.9, 123.6, 130.3, 136.7, 146.2, 149.8, 149.9, 151.3, 152.9, 154.5.MS (ESI): m/z = 468.0 [M + H]+.A solution of 2, 4-dichloro-5-methoxyaniline (1.9 g, 10 mmol), pyridine hydrochloride (1.2 g, 10 mmol) and4-chloro-7-(3-chloro-propoxy) -6-methoxy-quinoline-3-carbonitrile (3.1 g, 10 mmol)Placed in sealed tube, Anhydrous 2-ethoxyethanol (30 mL) was added, The mixture was heated at 140 C for 2 hours.After completion of the reaction, After the reaction solution was cooled to room temperature, Diluted with water (500 mL)Dichloromethane extraction (250 mL X2), The organic phases were combined, Respectively, with water, Washed with a saturated saline solution, Dried over anhydrous sodium sulfate, filter, Concentrated under reduced pressure, Purified by column chromatography7-(3-chloro-propoxy) _4_ (2, 4-dichloro-5-methoxy-phenylamino)-6-methoxy-quinoline-3-carbonitrile(Gray solid, 3.0 g), Yield 67%.

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