3-(3-Amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile → 3-(2-Amino-5-methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile

HRID 970996Notes

Reaction equation

HRID 970996 reaction equation
NC1C=C(C(C2C=CC(OC)=C(OC)C=2)=CC#N)C=CC=1OC.[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([N+:48]([O-])=O)=[C:30]([C:32]([C:36]2[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44][CH3:45])=[C:38]([O:46][CH3:47])[CH:37]=2)=[CH:33][C:34]#[N:35])[CH:31]=1>[Pd]>[NH2:48][C:29]1[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[CH:31][C:30]=1[C:32]([C:36]1[CH:37]=[C:38]([O:46][CH3:47])[C:39]([O:44][CH3:45])=[C:40]([O:42][CH3:43])[CH:41]=1)=[CH:33][C:34]#[N:35]

Participants

4

Reactant 2

HCID 689400613-(3-Amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrileHCID 692047053-(5-Methoxy-2-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile

Product 1

HCID 692053333-(2-Amino-5-methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrileYield 25%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-(2-Amino-5-methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile was prepared analogously to 3-(3-amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile using 3-(5-methoxy-2-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile (1.5 g, 4.0 mmol) and 10% Pd/C (0.2 g). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 85:15) to afford a single isomer of 3-(2-amino-5-methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile (0.3 g, 25%) as a yellow solid: mp 132-134° C.; 1H NMR (CDCl3) δ 6.87-6.82 (dd, J=3, 8 Hz, 1H), 6.81 (s, 2H), 6.68 (d, J=2 Hz, 1H), 6.64 (d, J=8.8 Ha, 1H), 5.58 (s, 1H), 3.90 (s, 3H), 3.83 (s, 6H), 3.77 (s, 3H), 3.28 (b, 2H); 13C NMR (CDCl3) δ 161.09, 153.38, 152.40, 140.15, 138.26, 131.07, 125.44, 117.94, 117.84, 117.24, 115.55, 106.15, 96.46, 60.95, 55.79, 55.32; Anal Calcd for C19H20N2O4: C, 67.05; H, 5.92; N, 8.23. Found: C, 67.02; H, 6.02; N, 8.07.

Workup

  1. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 85:15)

Sources & evidence

ORD record
ord-d2d612fb78794387b8f5370048c20942
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

Loading…