Diethylamine → 4-[(Diethylamino)methyl]benzoic acid

HRID 488541

Reaction equation

HRID 488541 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13]>C(#N)C>[CH2:12]([N:14]([CH2:15][CH3:16])[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)[CH3:13]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 742344-(Chloromethyl)benzoic acid

Product 1

HCID 9485164-[(Diethylamino)methyl]benzoic acidYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1 g (1 equivalent) of α-chloroparatoluic acid and 1.22 mL (2 equivalents) of diethylamine are placed in solution in 30 mL of acetonitrile. The reaction mixture is taken to reflux for 48 hours. The solvent is evaporated off under vacuum and the residue is purified by chromatography on silica gel column (CH2Cl2/MeOH 60/40 then pure MeOH). The product is obtained in the form of a white powder after precipitation from hexane. (Yield=63%).

Workup

  1. temperatureto reflux for 48 hours
  2. customThe solvent is evaporated off under vacuum
  3. customthe residue is purified by chromatography on silica gel column (CH2Cl2/MeOH 60/40
  4. customThe product is obtained in the form of a white powder
  5. customafter precipitation from hexane

Sources & evidence

ORD record
ord-67b3606ed97745088224a32eb7d53c20
Source dataset
uspto-grants-2005_12
Patent number
US06972343B1

Linked notes

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