Ethyl Acetate → Methyl 4-[(methylamino)methyl]benzoate

HRID 415173Notes

Reaction equation

HRID 415173 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.C(OCC)(=O)C.C(O)C.[CH3:22][NH2:23]>>[CH3:22][NH:23][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 22028356Methylamine ethanol

Product 1

HCID 11194668Methyl 4-[(methylamino)methyl]benzoateYield 74.4%

Procedure

Methyl 4-(bromomethyl)benzoate was dissolved in methylamine ethanol solution and the mixture was stirred at reflux for 3 hr. The mixture was condensed under vacuum and poured into ethyl acetate and filtered. The cake was dried to get methyl 4-((methylamino)methyl)benzoate (2.5 g, 74.4%), LC-MS (ESI) m/e 180 [M+1]−.

Workup

  1. temperatureat reflux for 3 hr
  2. customcondensed under vacuum
  3. filtrationfiltered
  4. customThe cake was dried

Sources & evidence

ORD record
ord-163fb8e25e924cd9b56f6f6711c3faf3
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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