2-Amino-5-iodobenzonitrile → 2-Amino-5-(3'-methoxybenzyl)benzonitrile

HRID 853758Notes

Reaction equation

HRID 853758 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][CH:21]=1)[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][CH:21]=[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 178490226HCID 178490226, compound

Product 1

HCID 109444792-Amino-5-(3'-methoxybenzyl)benzonitrile

Procedure

From 9 (488 mg, 2 mmol) and 3-methoxybenzylzinc chloride (0.5 M in THF, 10 mL, 5 mmol) by the same method as 10a; white powder (274 mg, 49%): mp 81-82° C.; 1H NMR (CDCl3) δ 3.81 (s, 2H, OMe), 3.82 (s, 2H, CH2), 4.25 (br s, NH2), 6.67 (d, J=8.0 Hz, 1H, H-3), 6.68 (s, 1H, H-2′), 6.72-6.77 (m, 2H, H4′ and H-6′), 7.15 (d, J=8.0 Hz, H-4), 7.19 (s, 1H, H-6), 7.22 (t, J=7.6 Hz, 1H, H-5′).

Sources & evidence

ORD record
ord-ba6055fa2e6c4b5b90f5cd8bbb14afcd
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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