2-Amino-5-iodobenzonitrile → 2-Amino-5-(2'-methoxybenzyl)benzonitrile

HRID 853757Notes

Reaction equation

HRID 853757 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:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][Zn+].NC1C=CC(CC2C=CC=CC=2)=CC=1C#N>>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[O:13][CH3:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 99648032-Amino-5-iodobenzonitrileHCID 109436972-Amino-5-benzylbenzonitrileHCID 178489474HCID 178489474, compound

Product 1

HCID 118066952-Amino-5-(2'-methoxybenzyl)benzonitrile

Procedure

From 9 (610 mg, 2.5 mmol) and 2-methoxybenzylzinc chloride (0.5 M in THF, 10 mL, 5 mmol) by the same method as 10a; white powder (364 mg, 61%): mp 77.5-78.5° C.; 1H NMR (CDCl3) δ 3.81 (s, 3H, OMe), 3.82 (s, 2H, CH2), 4.25 (br s, 2H, NH2), 6.64 (d, J=8.0 Hz, 1H, H-3), 6.85-6.88 (m, 2H, H-3′ and H-5′), 7.06 (d, J=7.2 Hz, 1H, H-6′), 7.18-7.23 (m, 3H, H-4′, H-4, and H-6).

Sources & evidence

ORD record
ord-981ec740c5164524a91848f00f795ef9
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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