Potassium Carbonate → HCID 22988090, compound

HRID 986996Notes

Reaction equation

HRID 986996 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:24][CH3:25])=[C:9]([C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[O:26]([C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:25][O:24][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([O:39][C:36]3[CH:35]=[CH:34][C:33]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:38][CH:37]=3)=[CH:3][CH:4]=[N:5]2)=[CH:10][C:9]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 22988091HCID 22988091, compound

Product 1

HCID 22988090HCID 22988090, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-7-methoxy-N-(3-morpholinopropyl)quinoline-6-carboxamide (0.154 g), 4-phenoxyphenol (0.11 g), potassium carbonate (0.207 g) and DMF (4 ml) was stirred and heated to 100° C. for 16 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The aqueous phase was further extracted with ethyl acetate and the combined organic extracts were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.13 g); NMR Spectrum: (CDCl3) 1.86 (m, 2H), 2.47 (m, 6H), 3.6 (m, 2H), 3.7 (m, 4H), 4.11 (s, 3H), 6.48 (d, 1H), 7.04-7.18 (m, 7H), 7.37 (m, 2H), 7.51 (s, 1H), 8.02 (t, 1H), 8.65 (d, 1H), 9.19 (s, 1H); Mass Spectrum M+H+ 514.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was further extracted with ethyl acetate
  4. washthe combined organic extracts were washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica using
  8. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-b6b4aafb1a014c899e8f8e613a7c21e6
Source dataset
uspto-grants-2003_10
Patent number
US06630489B1

Reaction notes

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