Dimethylamine, hydrochloride → Methyl 2-chloro-5-(dimethylamino)benzoate

HRID 1041876Notes

Reaction equation

HRID 1041876 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:5]=1[Cl:11].Cl.[CH3:14][NH:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([N:15]([CH3:16])[CH3:14])[CH:7]=[CH:6][C:5]=1[Cl:11]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 23331706Methyl 2-chloro-5-fluorobenzoate

Product 1

HCID 66909163Methyl 2-chloro-5-(dimethylamino)benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 4.00 g (20.6 mmol) 2-Chloro-5-fluoro-benzoic acid methyl ester (Rarechem) and 60 ml dimethylsulphoxid were added 2.03 g (24.7 mmol) dimethylamine hydrochloride and 5.97 g (43.2 mmol) potassium carbonate. The reaction mixture was stirred over night and was reduced with high vacuum rotation evaporator at 65° C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude product 18a was obtained in 99% yield (4.46 g, 20.9 mmol) and was used for the next step without purification.

Workup

  1. customwas reduced with high vacuum rotation evaporator at 65° C
  2. additionThe residue was diluted with dichloromethane
  3. washwashed twice with water
  4. extractionThe combined water phases were extracted with dichloromethane
  5. washThe combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d4d598219c9249ab87fe28f2897e558a
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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