Ammonia → N1-Isopropyl-N1-(4-methoxyphenyl)glycinamide

HRID 2117263Notes

Reaction equation

HRID 2117263 reaction equation
Br[CH2:2][C:3]([N:5]([CH:14]([CH3:16])[CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[O:4].[NH3:17]>CO>[CH:14]([N:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[C:3](=[O:4])[CH2:2][NH2:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 107795342-Bromo-N-isopropyl-N-(4-methoxyphenyl)acetamide

Product 1

HCID 54496521N1-Isopropyl-N1-(4-methoxyphenyl)glycinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromo-N-isopropyl-N-(4-methoxyphenyl)acetamide (1e, 2.86 g) was dissolved in methanol saturated with ammonia at 0° C. and left for 3 days at room temperature in a sealed flask. Methanol and ammonia were removed in vacuo and the residue was dissolved in chloroform (100 ml) and washed with water (2×50 ml). The organic layer was separated and dried with anhydrous MgSO4 and concentrated in vacuo to afford the titled product (1f, 2.7 g). 1H NMR (300 MHz, CDCl3) 6.96 (m, 4H), 4.99 (sept., J=6.6 Hz, 1H), 3.84 (s, 3H), 2.97 (s, 2H), 1.58 (s, 2H), 1.05 (d, J=6.6 Hz, 6H),

Workup

  1. customMethanol and ammonia were removed in vacuo
  2. dissolutionthe residue was dissolved in chloroform (100 ml)
  3. washwashed with water (2×50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05f222b69f164aa7834a0164a67752dc
Source dataset
uspto-grants-2008_10
Patent number
US07442693B2

Reaction notes

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