2-Chloro-3-iodo-5-nitropyridine → 5-Amino-2-chloro-3-iodopyridine

HRID 723714Notes

Reaction equation

HRID 723714 reaction equation
[Cl:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>[Fe]>[NH2:9][C:5]1[CH:6]=[C:7]([I:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

3

Reactant 1

HCID 111406392-Chloro-3-iodo-5-nitropyridine

Product 1

HCID 109012035-Amino-2-chloro-3-iodopyridineYield 77%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

2-Chloro-3-iodo-5-nitropyridine (0.25g, 0.88 mmol) was reacted with iron powder (0.25g, 4.4 mmol) in the manner described in example 762D. Removal of the solvent in vacuo gave compound 765C (0.172g, 77%), as a golden yellow solid. HPLC: 100% at 2.32 min(YMC S5 ODS column) eluting with 10–90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 255.03 [M+H]+.

Workup

  1. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-295b686205bd400bb52d5482937c0595
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

Loading…