2-Amino-5-iodobenzonitrile → 2-Amino-5-(4'-chlorobenzyl)benzonitrile

HRID 853754Notes

Reaction equation

HRID 853754 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][C:16]([CH2:17][Zn+])=[CH:15][CH:14]=1.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:13]([Cl:12])=[CH:14][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 178478120HCID 178478120, compound

Product 1

HCID 111284922-Amino-5-(4'-chlorobenzyl)benzonitrile

Procedure

From 9 (488 mg, 2 mmol) and 4-chlorobenzylzinc chloride (0.5 M in THF, 10 mL, 5 mmol) by the same method as 10a; white powder (243 mg, 59%): mp 91.5-93° C.; 1H NMR (DMSO-d6) δ 3.79 (s, 2H, CH2), 5.87 (br s, 2H, NH2), 6.68 (d, J=8.0 Hz, 1H, H-3), 7.11 (d, J=8.0 Hz, H-4), 7.18 (d, J=8.4 Hz, 2H, H-2′ and H-6′), 7.20 (s, 1, H-6),7.29 (d, J=8.4 Hz, 2H, H-3′ and H-5′).

Sources & evidence

ORD record
ord-7f34a2c63a654f35bb50848b9c7e9427
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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