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

HRID 2075942

Reaction equation

HRID 2075942 reaction equation
N#N.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:34][CH2:35][C:36]([OH:38])=O)[CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31].[N+:39]([C:42]1[CH:43]=[C:44]([NH2:48])[CH:45]=[CH:46][CH:47]=1)([O-:41])=[O:40]>ClCCl.CN(C1C=CN=CC=1)C>[N+:39]([C:42]1[CH:43]=[C:44]([NH:48][C:36](=[O:38])[CH2:35][CH2:34][C:26]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=2)[CH:45]=[CH:46][CH:47]=1)([O-:41])=[O:40]

Participants

8

Reactant 5

HCID 947NitrogenHCID 74233-NitroanilineHCID 8471TriethylamineHCID 648603,4,5-Trimethoxyhydrocinnamic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 9411047N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamideYield 70.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(The following reaction is done in an anhydrous N2 atmosphere.) Suspend EDC hydrochloride (402 mg, 2.10 mmol) and Et3N (293 μL, 2.10 mmol) in anhydrous dichloromethane (17.0 mL) and stir the resulting solution for 5 min at rt. Add 3-(3,4,5-trimethoxy-phenyl)-propionic acid (481 mg, 2.00 mmol) and DMAP (24 mg, 0.20 mmol) and stir the resulting solution for 5 min. Add 3-nitro-phenylamine (90) (414 mg, 3.00 mmol) and stir the reaction solution 24 h at rt. Quench reaction solution with sat. aqu. NH4Cl and water, separate layers and extract aqu. layer with EtOAc (3 times). Wash the combined organic layer with water and brine and dry with Na2SO4. Purify the crude product by preparative radial chromatography (silica gel 60 PF, EtOAc/CyH 1+1) to obtain N-(3-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide (91) (508 mg, 70%) as a yellowish solid. 1H NMR (400 MHz, CDCl3): 2.65 (t, 2H, J=7.3 Hz); 2.98 (t, 2H, J=7.3 Hz); 3.79 (s, 6H); 3.81 (s, 3H), 6.42 (s, 2H); 7.41 (s, 1H); 7.45 (t, 1H, J=8.0 Hz); 7.84 (d, 1H, J=8.0 Hz); 7.92 (d, 1H, J=8.0 Hz); 8.31 (s, 1H).

Workup

  1. custom(The following reaction
  2. customQuench
  3. customreaction solution with sat. aqu
  4. customNH4Cl and water, separate layers
  5. extractionextract aqu
  6. washWash the combined organic layer with water and brine
  7. dry with materialdry with Na2SO4
  8. customPurify the crude product by preparative radial chromatography (silica gel 60 PF, EtOAc/CyH 1+1)

Sources & evidence

ORD record
ord-6573d147a3de4e2993faaf4c262d7a43
Source dataset
uspto-grants-2011_04
Patent number
US07923473B2

Linked notes

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