Zinc → HCID 178492583, compound

HRID 853759Notes

Reaction equation

HRID 853759 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5][Cl:6].[Zn:13].NC1C=CC(I)=CC=1C#N>C1COCC1>[Cl-:6].[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5][Zn+:13]

Participants

5

Reactant 3

HCID 23994ZincHCID 2911942,5-Dimethoxybenzyl chlorideHCID 99648032-Amino-5-iodobenzonitrile

Product 1

HCID 178492583HCID 178492583, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Dimethoxybenzylzinc chloride was prepared from 2,5-dimethoxybenzyl chloride (746 mg, 4 mmol) and reactive metallic zinc suspension (0.76 M in THF, 6.3 mL, 4.8 mmol). The supernatant was transferred via a cannula into a solution of 9 (366 g, 1.5 mmol) in THF, followed by the usual workup; pale-yellow powder (280 mg, 69%): mp 90-92° C.; 1H NMR (CDCl3) δ 3.74 (s, 3H, OMe), 3.76 (s, 3H, OMe), 3.80 (s, 2H, CH2), 4.66 (br s, 2H, NH2), 6.63 (d, 1H, J=2.8 Hz, H-6′), 6.70 (d, J=8.4 Hz, 1H, H-3), 6.72 (dd, J=9.0 Hz, J=2.8 Hz, 1H, H4′), 6.80 (d, J=9.0 Hz, 1H, H-3;), 7.19 (d, J=8.4 Hz, 1H, H-4), 7.22 (s, 1H, H-6).

Sources & evidence

ORD record
ord-019ee2a37c3249cbbc7cfb36fe0209a7
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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