Methanol → Methyl 2-((4-hydroxyphenyl)amino)acetate

HRID 398023

Reaction equation

HRID 398023 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH3:13]O>>[CH3:13][O:11][C:10](=[O:12])[CH2:9][NH:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 67149N-(4-Hydroxyphenyl)glycine

Product 1

HCID 422581Methyl 2-((4-hydroxyphenyl)amino)acetateYield 99%

Procedure

The p-hydroxy phenyl glycine (74.0 g, 442 mmol) was suspended in methanol (500 mL), cooled in an ice bath and HCl (gas) was bubbled through the reaction mixture for 20 minutes, to give a clear solution. The reaction was stirred at rt for 48 h, concentrated in vacuo to give an oil which was triturated with ethyl ether to give the p-hydroxy phenyl glycine methyl ester (95.8 g, 99%) as a white powder. MS found: (M+H)+=182.

Workup

  1. temperaturecooled in an ice bath
  2. customHCl (gas) was bubbled through the reaction mixture for 20 minutes
  3. customto give a clear solution
  4. concentrationconcentrated in vacuo
  5. customto give an oil which
  6. customwas triturated with ethyl ether

Sources & evidence

ORD record
ord-49d8304cdbec4ea2a75f2c2f5b3084f4
Source dataset
uspto-grants-2003_08
Patent number
US06610731B2

Linked notes

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