Ammonium Hydroxide → 4-(Aminomethyl)-6-(1,1-dimethylethyl)-2-iodo-3-pyridinol

HRID 1112721Notes

Reaction equation

HRID 1112721 reaction equation
[I:1]Cl.Cl.Cl.[NH2:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:10]=[CH:9][C:8]=1[OH:17].[OH-].[NH4+]>Cl.O>[I:1][C:9]1[C:8]([OH:17])=[C:7]([CH2:6][NH2:5])[CH:12]=[C:11]([C:13]([CH3:14])([CH3:16])[CH3:15])[N:10]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24640Iodine chlorideHCID 126342623-Pyridinol, 4-(aminomethyl)-6-(1,1-dimethylethyl)-, hydrochloride (1:2)

Product 1

HCID 1943074-(Aminomethyl)-6-(1,1-dimethylethyl)-2-iodo-3-pyridinolYield 78.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of iodine monochloride (2.68 g., 0.02 mole) in 4N hydrochloric acid (15 ml.) is added to a solution of 4-aminomethyl-6-(1,1-dimethylethyl)-3-pyridinol . dihydrochloride (5.06 g., 0.02 mole) in water (30 ml.). The resulting solution is kept at 20°-25° C. for 18 hours, diluted with water to a volume of 100 ml. and basicified with concentrated ammonium hydroxide (12 ml.) whereupon a solid is deposited. The solid is collected, washed with water and air-dried to give 2-iodo-4-aminomethyl-6-(1,1-dimethylethyl)-3-pyridinol (4.8g., 78%), m.p. 162°-165° C. Recrystallization of the latter from 50% ethanol provides an analytical sample of 2-iodo-4-aminomethyl-6-(1,1-dimethylethyl)-3-pyridinol as pale beige crystals, m.p. 170°-171° C.

Workup

  1. customThe solid is collected
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-103996e159a64c6bbcfa4c70331d4d61
Source dataset
uspto-grants-1978_10
Patent number
US04123537

Reaction notes

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