Iodine → 3-(3-Iodo-2-propynyloxy)-6-methylpyridine

HRID 27044Notes

Reaction equation

HRID 27044 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:4][CH:3]=1.CO.[OH-].[Na+].[I:16]I>O>[I:16][C:11]#[C:10][CH2:9][O:8][C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 807IodineHCID 887MethanolHCID 14798Sodium HydroxideHCID 233434956-Methyl-3-(2-propynyloxy)-pyridine

Product 1

HCID 233434813-(3-Iodo-2-propynyloxy)-6-methylpyridineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 160 g (1.10 moles) 6-methyl-3-(2-propynyloxy)pyridine and 2000 ml methanol was cooled to 0° C. and 750 g 25% sodium hydroxide solution was slowly added. Iodine (362 g, 1.4 moles) was added portionwise and the resulting suspension stirred at 0°-10° C. for an additional 30 min. The reaction mixture was then poured into 4000 ml water and the solids filtered to give 250 g 3-(3-iodo-2-propynyloxy)-6-methylpyridine. Yield=90% Recrystallization from methanol gave analytically pure material, mp 155°-157° C.

Workup

  1. filtrationthe solids filtered

Sources & evidence

ORD record
ord-6f02a6cc4ff649ab92d9c789d188e421
Source dataset
uspto-grants-1980_09
Patent number
US04220577

Reaction notes

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