Nitrogen → N-(3-Amino-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide

HRID 383616

Reaction equation

HRID 383616 reaction equation
N#N.[N+:3]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:28])[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)[CH:9]=[CH:10][CH:11]=1)([O-])=O>CO.[Pd]>[NH2:3][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:28])[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 9411047N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide

Product 1

HCID 16225054N-(3-Amino-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

(The following reaction is done in an N2 atmosphere.) Dissolve N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide (89) (100 mg, 0.28 mmol) in MeOH (4.5 mL) and add Pd on carbon (10% (w/w) Pd content, 29.5 mg, 0.028 mmol) followed by NH4CO2H (175 mg, 2.77 mmol) at rt. Degas the reaction mixture carefully (flush with N2) and stir it for 75 min at rt. Filtrate reaction mixture through a short pad of celite and remove solvent. Treat residue with EtOAc, filtrate again through a short pad of celite and remove solvent to obtain N-(3-Amino-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide (90) (91 mg, 99%) as a white solid. No further purification. 1H NMR (400 MHz, CD3OD): 2.65 (t, 2H, J=7.5 Hz); 2.98 (t, 2H, J=7.5 Hz); 3.75 (s, 3H); 3.82 (s, 6H); 6.50 (dd, 1H, J1=8.0 Hz, J2=2.0 Hz); 6.58 (s, 2H); 6.80 (dd, 1H, J=8.0 Hz, J2=2.0 Hz); 7.02-7.07 (m, 1H); 7.04 (t, 1H, J=8.0 Hz).

Workup

  1. custom(The following reaction
  2. customfollowed by NH4CO2H (175 mg, 2.77 mmol) at rt
  3. customDegas
  4. customthe reaction mixture carefully (flush with N2)
  5. customFiltrate reaction mixture through a short pad of celite
  6. customremove solvent
  7. customTreat residue with EtOAc, filtrate again through a short pad of celite and remove solvent

Sources & evidence

ORD record
ord-9ede8fb8e0f041c595165695f309931d
Source dataset
uspto-grants-2013_02
Patent number
US08367677B2

Linked notes

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