Dimethylamine, hydrochloride → 3-Cyano-4-dimethylamino-benzoic acid methyl ester

HRID 1041854Notes

Reaction equation

HRID 1041854 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([C:11]#[N:12])[CH:5]=1.Cl.[CH3:15][NH:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([N:16]([CH3:17])[CH3:15])=[C:6]([C:11]#[N:12])[CH:5]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 45790123Methyl 3-cyano-4-fluorobenzoate

Product 1

HCID 598476573-Cyano-4-dimethylamino-benzoic acid methyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 24.0 g (134 mmol) 2b and 240 ml dimethylsulphoxid were added 13.2 g (161 mmol) dimethylamine hydrochloride and 38.9 g (281 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 2c was obtained in 94% yield (25.7 g, 126 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-bde7369ec99c49e4b3d9d1a2bab9a9ac
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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