Potassium Carbonate → Methyl 2-chloro-4-(cyclopropylmethylamino)benzoate

HRID 406393Notes

Reaction equation

HRID 406393 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[CH:22]=[C:21](F)[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]>O>[Cl:12][C:13]1[CH:22]=[C:21]([NH:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75646CyclopropanemethanamineHCID 2763551Methyl 2-Chloro-4-fluorobenzoate

Product 1

HCID 66779311Methyl 2-chloro-4-(cyclopropylmethylamino)benzoateYield 96.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyclopropylmethylamine (1.51 g) and potassium carbonate (1.46 g) were added to a solution of methyl 2-chloro-4-fluorobenzoate (1.00 g). The reaction mixture was stirred at room temperature for 6 hours and then heated with stirring at 100° C. for 6 hours under a microwave reactor. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.23 g).

Workup

  1. temperatureheated
  2. stirringwith stirring at 100° C. for 6 hours under a microwave reactor
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b8b59f4dce2c406d87b6d3ee1453c975
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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