Dimethylformamide → Methyl 4-(4-amino-3-chlorophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate

HRID 1010248Notes

Reaction equation

HRID 1010248 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:23]=1[Cl:29].[H-].[Na+].CN(C)C=O>O>[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:24][C:23]=1[Cl:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 871844-Amino-3-chlorophenolHCID 22936872Methyl 4-chloro-7-(2-methoxyethoxy)-6-quinolinecarboxylate

Product 1

HCID 22936947Methyl 4-(4-amino-3-chlorophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-chloro-7-(2-methoxyethoxy)-6-quinolinecarboxylate (4.9 g), 4-amino-3-chlorophenol (2.0 g), sodium hydride (550 mg) and dimethylformamide (20 ml) were stirred together at 100° C. for 2 hours. The mixture was returned to room temperature, water was added, and extraction was performed with ethyl acetate. Silica gel was added to the extract solution and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (hexane:ethyl acetate=1:1, followed by ethyl acetate) to obtain 3.2 g of the target substance as a violet solid.

Workup

  1. customwas returned to room temperature
  2. extractionextraction
  3. additionSilica gel was added to the extract solution
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompacked with silica gel, and purification
  7. customto obtain 3.2 g of the target substance as a violet solid

Sources & evidence

ORD record
ord-078f2e351faa4a31adad38c2df161330
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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