Ammonium Hydroxide → 4-Iodo-5-methylpyridin-2-amine

HRID 1748198Notes

Reaction equation

HRID 1748198 reaction equation
F[C:2]1[CH:7]=[C:6]([I:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[OH-].[NH4+:11]>>[I:8][C:6]1[C:5]([CH3:9])=[CH:4][N:3]=[C:2]([NH2:11])[CH:7]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 100600522-Fluoro-4-iodo-5-methylpyridine

Product 1

HCID 667478634-Iodo-5-methylpyridin-2-amine

Conditions

Temperature
110 °C

Procedure

In a 500 mL sealed tube 2-fluoro-4-iodo-5-methylpyridine (4.0 g, 16.81 mmol) in 12N ammonium hydroxide (300 mL) was heated to 110° C. for 72 hours. Upon cooling to room temperature a white solid separated. The solid was collected, washed with water and dried in vacuo to afford 4-iodo-5-methylpyridin-2-amine (I-28A) as an off-white solid which was carried on to the next step without purification. 1H-NMR (400 MHz, CDCl3) δ 7.82 (s, 1H), 7.04 (s, 1H), 4.27 (bs, 2H), 2.24 (s, 3H). MS m/z 235.0 (M+1).

Workup

  1. temperatureUpon cooling to room temperature a white solid
  2. customseparated
  3. customThe solid was collected
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-10579090532e4283b27982d471c527da
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

Loading…