Methylamine → HCID 19745954, compound

HRID 2253613Notes

Reaction equation

HRID 2253613 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:15]([CH3:21])[C:16](OCC)=[O:17])[CH:8]=[CH:9][C:10]=1[O:11]C(=O)C)(=O)C.[CH3:22][NH2:23]>>[CH3:22][NH:23][C:16](=[O:17])[CH:15]([C:7]1[CH:8]=[CH:9][C:10]([OH:11])=[C:5]([OH:4])[CH:6]=1)[CH3:21]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 67829686HCID 67829686, compound

Product 1

HCID 19745954HCID 19745954, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 2 g of ethyl 3,4-diacetoxyphenylpropionate and 2.1 g of a 40% aqueous methylamine solution was heated to 150° C. with stirring for 2 hours in an autoclave. After cooling, the reaction mixture was acidified, extracted three times with 25 ml of ethyl acetate and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by column chromatography using silica gel. A solvent mixture of chloroform:methanol=20:1 was used as eluent. Pure N-methyl-3,4-dihydroxyphenylpropionamide thus obtained was 0.35 g.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with 25 ml of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by column chromatography
  6. additionA solvent mixture of chloroform

Sources & evidence

ORD record
ord-af7cad2a92034a5a910c351763049a51
Source dataset
uspto-grants-1993_08
Patent number
US05232923

Reaction notes

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