Potassium Iodide → HCID 23325020, compound

HRID 1153744Notes

Reaction equation

HRID 1153744 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-a28f12197d564dff96ae303acec09e09
Source dataset
uspto-grants-1984_12
Patent number
US04486434

Reaction notes

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