N-Iodosuccinimide → 6-hydroxy-5-iodo-2-oxo-1H-pyridine-3-carboxamide

HRID 2284491Notes

Reaction equation

HRID 2284491 reaction equation
[OH:1][C:2]1[N:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C1C(=O)N([I:19])C(=O)C1>C(Cl)Cl>[OH:1][C:2]1[N:10]=[C:9]([OH:11])[C:8]([I:19])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178513675HCID 178513675, compound

Product 1

HCID 1785136806-hydroxy-5-iodo-2-oxo-1H-pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 2,6-dihydroxynicotinamide (20 g, 0.13 mol) and NIS (29.2 g, 0.13 mol) in DCM (1000 mL) was stirred at r.t for 20 min. The mixture was concentrated in vacuo to afford crude compound 2,6-dihydroxy-5-iodonicotinamide. (50 g) which was used for the next step directly. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 11.04 (bs, 1H), 8.46 (s, 1H), 2.55 (s, 4H).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-86af918945c9468a95a6c570d8d4d3b7
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Reaction notes

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