HCID 69202502, compound → HCID 69202478, compound

HRID 2378250Notes

Reaction equation

HRID 2378250 reaction equation
NC1C=C(C(C2C=CC(OC)=C(OCC)C=2)=CC#N)C=CC=1OC.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:36]([C:40]2[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=[C:42]([O:48][CH3:49])[CH:41]=2)=[CH:37][C:38]#[N:39])[CH:30]=[CH:31][C:32]=1[N+:33]([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>>[NH2:33][C:32]1[CH:31]=[CH:30][C:29]([C:36]([C:40]2[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=[C:42]([O:48][CH3:49])[CH:41]=2)=[CH:37][C:38]#[N:39])=[CH:28][C:27]=1[O:26][CH3:25]

Participants

4

Reactant 3

HCID 69202502HCID 69202502, compoundHCID 69204282HCID 69204282, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 69202478HCID 69202478, compoundYield 86.9%

Procedure

3-(4-Amino-3-methoxy-phenyl)-3-(3,5-dimethoxy-phenyl)-acrylonitrile was prepared analogously to 3-(3-amino-4-methoxy-phenyl)-3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile using 3-(3-methoxy-4-nitro-phenyl)-3-(3,5-dimethoxy-phenyl)-acrylonitrile (3.9 g, 11.5 mmol) and tin chloride dihydrate (12.8 g, 58.0 mmol) to afford mixture isomers of 3-(4-amino-3-methoxy-phenyl)-3-(3,5-dimethoxy-phenyl)-acrylonitrile (3.1 g, 84%) as a yellow solid: mp 114-116° c; 1H NMR (CDCl3) δ 7.04-6.45 (m, 6H), 5.60(5.46) (s, 1H), 3.86-3.70 (m, 11H); 13C NMR (CDCl3) δ 163.18, 162.98, 160.57, 146.32, 142.06, 139.34, 139.07, 138.57, 128.03, 126.37, 124.00, 122.74, 107.15, 102.02, 101.95, 91.86, 90.98, 55.69, 55.55; Anal Calcd for C18H18N2O3: C, 69.66; H, 5.85; N, 9.03. Found: C, 69.33; H, 5.67; 8.85.

Sources & evidence

ORD record
ord-9b46eeb332754ce9b4413fcedd8fb37a
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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