4-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile → 4-(6-Chloro-2,3-methylenedioxyanilino)-7-(3-chloropropoxy)-3-cyano-6-methoxyquinoline

HRID 1784095Notes

Reaction equation

HRID 1784095 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Na].[Cl:11][C:12]1[C:17]([NH2:18])=[C:16]2[O:19][CH2:20][O:21][C:15]2=[CH:14][CH:13]=1.Cl[C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][Cl:39])=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][C:24]=1[C:40]#[N:41]>CN(C=O)C.O>[Cl:11][C:12]1[C:17]([NH:18][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][Cl:39])=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][C:24]=2[C:40]#[N:41])=[C:16]2[O:19][CH2:20][O:21][C:15]2=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 112206374-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrileHCID 113672535-Chloro-1,3-benzodioxol-4-amineHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 98681694-(6-Chloro-2,3-methylenedioxyanilino)-7-(3-chloropropoxy)-3-cyano-6-methoxyquinolineYield 86.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hexamethyldisilazane (1M solution in THF; 3.34 ml) was added to a solution of 6-chloro-2,3-methylenedioxyaniline (0.573 g) in DMF (12 ml) that was cooled to 0° C. and the mixture was stirred for 5 minutes. A solution of 4-chloro-7-(3-chloropropoxy)-3-cyano-6-methoxyquinoline (0.5 g) in DMF (3 ml) was added and the resultant mixture was stirred at ambient temperature for 1 hour. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica increasingly polar mixtures of methylene chloride and ethyl acetate as eluent. There was thus obtained the title compound as a solid (0.62 g); NMR Spectrum: DMSOd6 at 60° C.) 2.32 (m, 2H), 3.9 (m, 2H), 4.0 (s, 3H), 4.35 (m, 2H), 6.1 (s, 2H), 7.0 (d, 1H), 7.1 (d, 1H), 7.4 (s, 1H), 7.9 (s, 1H), 8.42 (s, 1H), 9.32 (s, 1H); Mass Spectrum: M+H+ 446 and 448.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water and with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica
  6. temperatureincreasingly polar mixtures of methylene chloride and ethyl acetate as eluent

Sources & evidence

ORD record
ord-f224ec6f8a7b411681d41b4cca8facae
Source dataset
uspto-grants-2009_03
Patent number
US07501516B2

Reaction notes

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