Potassium Iodide → HCID 23325020, compound

HRID 1381018Notes

Reaction equation

HRID 1381018 reaction equation
N[C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.N([O-])=O.[Na+].[I-:18].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O.O>[I:18][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 13094269HCID 13094269, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23325020HCID 23325020, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

5-Amino-2-[4-aminobutyl]-3-methylpyridine (2.17 g) in 20% sulphuric acid (25 ml) at -5° C. was reacted with a solution of sodium nitrite (1 g) in water (5 ml) over 20 minutes. After a further 15 minutes at -9° C. the reaction mixture was added to a mixture of potassium iodide (4 g) and cuprous iodide (0.5 g) in water (65 ml) at 10° C. and then stirred at room temperature for 30 minutes. Saturated sodium thiosulphate solution (10 ml) was added and the pH was brought to 12 with sodium hydroxide. Chloroform extraction of the reaction mixture gave 5-iodo-3-methyl-2-(4-aminobutyl)pyridine as a dark oil (2.45 g). N.M.R. (CDCL3) assignment, δ (p.p.m.), multiplicity; (CH2)2CH2NH2, 1.4-2.0, m; NH2, 1.69, s; 3-CH3, 2.28, s; CH2 (CH2)2CH2NH2, 2.76, m; 4-H pyridyl, 7.75, m; 6-H pyridyl, 8.57, m;

Workup

  1. extractionChloroform extraction of the reaction mixture

Sources & evidence

ORD record
ord-d22b97c60523499eab6c00b286ca90c4
Source dataset
uspto-grants-1986_04
Patent number
US04584381

Reaction notes

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