Methylamine → (E)-3-(5-Nitro-2-methoxy-phenyl)-N-methyl-acrylamide

HRID 47445Notes

Reaction equation

HRID 47445 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1/[CH:12]=[CH:13]/[C:14]([OH:16])=O.C[CH2:18][N:19]=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN>CN(C)C=O>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4](/[CH:12]=[CH:13]/[C:14]([NH:19][CH3:18])=[O:16])[CH:5]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64377452-Propenoic acid, 3-(2-methoxy-5-nitrophenyl)-

Product 1

HCID 22745125(E)-3-(5-Nitro-2-methoxy-phenyl)-N-methyl-acrylamideYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-3-(2-Methoxy-5-nitro-phenyl)-acrylic acid (Egypt. J. Pharm. Sci., (1996), 37, 71-84), (1.0 g) in dimethylformamide (5 ml) was treated with EDC.HCl (0.86 g), N-hydroxybenzotriazole (0.1 g) and methylamine (2M in tetrahydrofuran 3 ml) and stirred for 18 h. Solvent was removed at reduced pressure, the residue dissolved in dichloromethane, washed with 2N HCl, sodium hydrogen carbonate and brine. After drying (MgSO4), solvent was removed at reduced pressure and the residue column chromatographed (silica gel, 5% methanol:dichloromethane) to give the title compound (0.75 g). 1H NMR δ: 2.71 (3H, d, J=4.7Hz), 4.01 (3H, s), 6.71 (1H, d, J=15.9 Hz), 7.30 (1H, d, J=9.2 Hz), 7.62 (1H, d, J=15.9 Hz), 8.09 (1H, m), 8.25 (1H, dd, J=2.8, 9.2 Hz), 8.36 (1H, d, J=2.8 Hz).

Workup

  1. customSolvent was removed at reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with 2N HCl, sodium hydrogen carbonate and brine
  4. dry with materialAfter drying (MgSO4), solvent
  5. customwas removed at reduced pressure
  6. customthe residue column chromatographed (silica gel, 5% methanol:dichloromethane)

Sources & evidence

ORD record
ord-59d0a30c263f4ef0b08a6e4c2c5a5ea9
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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