N,N-dimethyl-4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide → N,N-dimethyl 4-amino-3-methylphenoxyacetamide

HRID 1584133Notes

Reaction equation

HRID 1584133 reaction equation
[CH3:1][N:2]([CH3:22])[C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(OC(C)(C)C)=O)=[C:8]([CH3:20])[CH:7]=1>FC(F)(F)C(O)=O>[CH3:22][N:2]([CH3:1])[C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([CH3:20])[CH:7]=1

Participants

3

Reactant 1

HCID 15870806N,N-dimethyl-4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide

Product 1

HCID 15870807N,N-dimethyl 4-amino-3-methylphenoxyacetamideYield 73.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a 200 mL round bottomed flask with a stirring bar and a drying tube was added N,N-dimethyl 4-(1,1-dimethylethoxycarbonyl)amino-3-methyphenoxyacetamide (1.00 g, 3.24 mmol) and trifluoroacetic acid (20 mL). This solution was stirred at ambient temperature 48 h. The trifluoroacetic acid was removed in vacuo and the residue was dissolved in 200 mL of EtOAc. This solution was washed with NaHCO3 solution and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave 0.493 g (73% yield) of N,N-dimethyl 4-amino-3-methylphenoxyacetamide as white crystals. 1H NMR (CDCl3): d 2.15 (s, 3H), 2.97 (s, 3H), 3.08 (s, 3H), 3.27 (br s, 2H), 4.59 (s, 2H), 6.71 (m, 3H). ##STR52## N,N-Dimethyl-2-(4-amino-3-methylphenoxy)ethylamine (5-4)

Workup

  1. customThe trifluoroacetic acid was removed in vacuo
  2. dissolutionthe residue was dissolved in 200 mL of EtOAc
  3. washThis solution was washed with NaHCO3 solution and brine
  4. customDrying
  5. filtration(MgSO4), filtration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-65de6b4fee5e49bc8336a46039e5ca1e
Source dataset
uspto-grants-1999_08
Patent number
US05932582

Reaction notes

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