Acetic Acid → Methyl [4-(aminomethyl)phenoxy]acetate acetate

HRID 733511Notes

Reaction equation

HRID 733511 reaction equation
O[N:2]=[CH:3][C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1.C(O)(=O)C.N#N>CO.[Pd]>[C:10]([OH:12])(=[O:11])[CH3:9].[NH2:2][CH2:3][C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 947NitrogenHCID 73461790Methyl {4-[(hydroxyimino)methyl]phenoxy}acetate

Product 1

HCID 86028338Methyl [4-(aminomethyl)phenoxy]acetate acetateYield 162.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl {4-[(hydroxyimino)methyl]phenoxy}acetate (30 g, 0.14 mol) in methanol (650 mL) was added glacial acetic acid (6.8 g) and passed N2 for 30 min. To this was added Pd/C (10%, 3 g) and hydrogenated under 2 bars of pressure for 12 h. The reaction mixture was concentrated under vacuum. The crude product was treated with EtOAc (500 mL) and the white product filtered off The solid was dried under vacuum to give the title compound (29 g, 81%).

Workup

  1. customfor 30 min
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionThe crude product was treated with EtOAc (500 mL)
  4. filtrationthe white product filtered off The solid
  5. customwas dried under vacuum

Sources & evidence

ORD record
ord-fb2be3a7a0ff46b7897414ab1a99b24c
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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