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

HRID 2186331Notes

Reaction equation

HRID 2186331 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-d38c97940bb74ce7a51ba33a9c2e98d7
Source dataset
uspto-grants-2002_06
Patent number
US06403632B1

Reaction notes

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