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

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:3]=1[C:4]#[N:5].[Cl-].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=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]=[C:13]([Cl:12])[CH:14]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Reactant 3

HCID 99648032-Amino-5-iodobenzonitrile

HCID 109436972-Amino-5-benzylbenzonitrile

HCID 178478087HCID 178478087, compound

Product 1

HCID 110859682-Amino-5-(3'-chlorobenzyl)benzonitrile

Procedure

From 9 (488 mg, 2 mmol) and 3-chlorobenzylzinc chloride (0.5 M in THF, 10 mL, 5 mmol) by the same method as 10a; white powder (269 mg, 55%): mp 84.5-85.5° C.; 1H NMR (CDCl3) δ 3.82 (s, 2H, CH2), 4.30 (br s, 2H, NH2), 7.02 (d, J=8.4 Hz, 1H, H-3), 7.12-7.22 (m, 5H, aromatic protons).

Sources & evidence

ORD record: ord-3028a0a8a895418290e4b5a9dad36525
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256197B2

Reaction notes

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