Hydrochloric Acid → 3-Cyano-7-ethoxy-6-methoxy-4-[4-(3-methoxyprop-1-ynyl)-2,3-methylenedioxyanilino]quinoline monohydrochloride salt

HRID 347426

Reaction equation

HRID 347426 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Na].[CH3:11][O:12][CH2:13][C:14]#[C:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]2[O:23][CH2:24][O:25][C:17]=12.[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([O:39][CH2:40][CH3:41])=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][C:28]=1[C:42]#[N:43].Cl>O.C(Cl)Cl.C(OCC)C.CN(C=O)C>[ClH:26].[C:42]([C:28]1[CH:29]=[N:30][C:31]2[C:36]([C:27]=1[NH:20][C:19]1[CH:21]=[CH:22][C:16]([C:15]#[C:14][CH2:13][O:12][CH3:11])=[C:17]3[O:25][CH2:24][O:23][C:18]=13)=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH2:40][CH3:41])[CH:32]=2)#[N:43]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrileHCID 210827034-(3-Methoxyprop-1-ynyl)-2,3-methylendioxyanilineHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 210826963-Cyano-7-ethoxy-6-methoxy-4-[4-(3-methoxyprop-1-ynyl)-2,3-methylenedioxyanilino]quinoline monohydrochloride saltYield 69.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hexamethyldisilazane (1M solution in THF; 1.17 ml) was added to a stirred mixture of 4-(3-methoxyprop-1-ynyl)-2,3-methylenedioxyaniline (0.12 g), 4-chloro-3-cyano-7-ethoxy-6-methoxyquinoline (0.146 g) and DMF (8 ml) that had been cooled to 0° C. and the resultant mixture was allowed to warm to ambient temperature and was stirred for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and with a saturated brine solution, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was dissolved in the minimum quantity of methylene chloride. The solution was diluted with diethyl ether and a solution of hydrogen chloride in diethyl ether (1M) was added. The resultant solid was isolated, washed with diethyl ether and dried. Thereby, the product was obtained the title compound (0.18 g); NMR Spectrum: (DMSOd6) 1.44 (t, 3H), 3.33 (s, 3H), 4.0 (s, 3H), 4.24 (q, 2H), 4.36 (s, 2H), 6.12 (s, 2H), 6.96 (d, 1H), 7.03 (d, 1H), 7.45 (s, 1H), 8.11 (s, 1H), 8.96 (s, 1H); Mass Spectrum: M+H+ 432.

Workup

  1. temperatureto warm to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and with a saturated brine solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica
  7. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  8. customThe material so obtained
  9. customThe resultant solid was isolated
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-bccc0d496dfa48beb370028bd827b56f
Source dataset
uspto-grants-2007_02
Patent number
US07173135B2

Linked notes

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