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

HRID 2110476Notes

Reaction equation

HRID 2110476 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 (0.25 g, 0.88 mmol) was reacted with iron powder (0.25 g, 4.4 mmol) in the manner described in example 762D. Removal of the solvent in vacuo gave compound 765C (0.172 g, 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-e5d2196bcf8d4072b8baf84c60c91652
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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