3-(3-Amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile → (3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanone

HRID 971037Notes

Reaction equation

HRID 971037 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:31]=[CH:30][C:29]([CH:32]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH2:43][CH3:44])[CH:35]=2)[OH:33])=[CH:28][C:27]=1[N+:45]([O-:47])=[O:46].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH2:43][CH3:44])[CH:35]=2)=[O:33])=[CH:28][C:27]=1[N+:45]([O-:47])=[O:46]

Participants

4

Reactant 3

HCID 689400613-(3-Amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrileHCID 69203000(3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 69204020(3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanoneYield 89%

Procedure

(4-Methoxy-3-nitro-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanone was prepared analogously to 3-(3-amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile using (4-methoxy-3-nitro-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol (3.9 g, 11.6 mmol) and pyridinium chlorochromate (3.7 g, 17.4 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 95:5) to afford (4-methoxy-3-nitro-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanone (3.4 g, 89%) as an orange solid: 1H NMR (CDCl3) δ 8.28 (d, J=2 Hz, 1H), 8.06-8.02 (dd, J=3, 8.7 Hz, 1H), 7.41 (d, J=1 Hz, 1H), 7.31-7.26 (dd, J=2, 8.4 Hz, 1H), 7.21 (d, J=8 Hz, 1H), 6.94 (d, J=8 Hz, 1H), 4.21-4.12 (q, J=7 Hz, 2H), 4.05 (s, 3H), 3.96 (s, 3H), 1.50 (t, J=6 Hz, 3H).

Workup

  1. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 95:5)

Sources & evidence

ORD record
ord-8adae18d6fdd4be1b00ff9c9ce0de8b8
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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