4-Ethenylbenzonitrile → HCID 178436434, compound

HRID 2069419Notes

Reaction equation

HRID 2069419 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:12][OH:13].C([O-])(O)=O.[Na+]>>[OH:13][NH:12][C:1](=[NH:2])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 769674-EthenylbenzonitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178436434HCID 178436434, compound

Procedure

4-Cyanostyrene is transformed to the corresponding hydroxyamidine according to literature procedures using hydroxylamine hydrochloride and NaHCO3 as base (e.g. E. Meyer, A. C. Joussef, H. Gallardo, Synthesis 2003, 899-905); LC-MS: tR=0.55 min; [M+H]+=163.04; 1H NMR (D4-methanol): δ 4.86 (s br, 3H), 5.30 (d, J=11.0 Hz, 1H), 5.85 (d, J=17.6 Hz, 1H), 6.77 (dd, J=17.6, 10.8 Hz, 1H), 7.48 (d, J=8.3 Hz, 2H), 7.63 (d, J=8.0 Hz, 2H).

Workup

  1. customGallardo, Synthesis 2003, 899-905)

Sources & evidence

ORD record
ord-88cdbe653cbb409c88becb88a6f1ad89
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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