2-Amino-5-iodobenzonitrile → 2-Amino-5-(3',4'-dimethoxybenzyl)benzonitrile

HRID 853760Notes

Reaction equation

HRID 853760 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:3]=1[C:4]#[N:5].[Cl-].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:17][Zn+].NC1C=CC(CC2C=CC=CC=2)=CC=1C#N>>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:17][C:16]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:14]([O:13][CH3:12])[CH:15]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 99648032-Amino-5-iodobenzonitrileHCID 109436972-Amino-5-benzylbenzonitrileHCID 178490614HCID 178490614, compound

Product 1

HCID 110867562-Amino-5-(3',4'-dimethoxybenzyl)benzonitrile

Procedure

From 9 (488 mg, 2 mmol) and 3,4-dimethoxybenzylzinc chloride (0.5 M in THF, 10 mL, 5.0 mmol) by the same method as 10a; yellow oil (247 mg, 46%): 1H NMR (CDCl3) δ 3.79 (s, 2H, CH2), 3.83 (s, 3H, OMe), 3.86 (s, 3H, OMe), 4.21 (br s, NH2), 6.65-6.82 (m, 4H, H-3, H-2′, H-5′, and H-6′), 7.15 (d, J=8.4 Hz, 1H, H-4),7.17 (s, 1H, H-6).

Sources & evidence

ORD record
ord-572419081ac547378b8e1bac98efc138
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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