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

HRID 853752Notes

Reaction equation

HRID 853752 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:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][Zn+].NC1C=CC(CC2C=CC=CC=2)=CC=1C#N>>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[Cl:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 99648032-Amino-5-iodobenzonitrileHCID 109436972-Amino-5-benzylbenzonitrileHCID 178478034HCID 178478034, compound

Product 1

HCID 109884742-Amino-5-(2'-chlorobenzyl)benzonitrile

Procedure

From 9 (488 mg, 2 mmol) and 2-chlorobenzylzinc chloride (0.5 Min THF, 10 mL, 5 mmol) by the same methods as 10a; white powder (272 mg, 62%), mp 79-80° C.; 1H NMR (CDCl3) δ 3.96 (s, 2H, CH2), 4.79 (br s, 2H, NH2), 6.69 (d, J=8.8 Hz, 1H, H-3), 7.12-7.19 (m, 5H, aromatic protons), 7.20 (s, 1H, H-6).

Sources & evidence

ORD record
ord-bc94ec9e475f45839350b6ffb7c0aaa1
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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