Sulfuric Acid → Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate

HRID 451223

Reaction equation

HRID 451223 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=O.[CH:17]1([C:20](=O)[CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:19][CH2:18]1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[CH:17]1([C:20]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:4]([C:6]3[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=3)[C:3]3[C:2](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:1]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 98372872-Amino-4'-fluorobenzophenoneHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Product 1

HCID 9901664Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To the solution of 2-amino-4′-fluorobenzophenone (100 g) in acetic acid (500 ml) added methyl 3-cyclopropyl-3-oxopropanoate (132 g), sulfuric acid (5 ml) and stirred for 15 minutes at 25° C. Heated the reaction mixture to 100° C. for 10 hrs. Cooled the reaction mixture to 0-5° C. and pH adjusted to neutral conditions with 40% sodium hydroxide solution. Filtered the solid formed and washed with water. The wet solid was dissolved in methylene chloride and separated the water from it. Silica slurry was given to the reaction mixture and filtered it. Methylene chloride was distilled off and the compound was co-distilled with methanol. To the compound added methanol (150 ml) and stirred for 1 hr at 25° C. Filtered the solid and washed with methanol (50 ml). Dried the obtained solid to get the title compound.

Workup

  1. temperatureHeated the reaction mixture to 100° C. for 10 hrs
  2. temperatureCooled the reaction mixture to 0-5° C.
  3. filtrationFiltered the solid
  4. customformed
  5. washwashed with water
  6. dissolutionThe wet solid was dissolved in methylene chloride
  7. customseparated the water from it
  8. filtrationfiltered it
  9. distillationMethylene chloride was distilled off
  10. additionTo the compound added methanol (150 ml)
  11. stirringstirred for 1 hr at 25° C
  12. filtrationFiltered the solid
  13. washwashed with methanol (50 ml)
  14. customDried the obtained solid

Sources & evidence

ORD record
ord-ae69e7d3151d4261bfbca8585104a86b
Source dataset
uspto-grants-2013_07
Patent number
US08487105B2

Linked notes

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