Ammonium Hydroxide → 2-Amino-5-chloro-3-fluoropyridine

HRID 2262679Notes

Reaction equation

HRID 2262679 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:9])[C:5](F)=[N:6][CH:7]=1.[OH-].[NH4+:11]>>[NH2:11][C:5]1[C:4]([F:9])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1

Participants

3

Conditions

Temperature
150 °C

Procedure

To a 20 mL microwave vial equipped with a stir bar was added 5-chloro-2,3-difluoropyridine (2.0 g, 41 mmol). Ammonium hydroxide (ca 12 mL) was then added and the mixture was stirred until homogeneous. The solution was capped and heated in the microwave reactor at 150° C. for three 20 minute increments until a white solid precipitated out of solution. The white solid was filtered, washed with water, and dried to afford 2-amino-5-chloro-3-fluoropyridine (1.5 g, 76% yield), characterized by 1H NMR (d6-DMSO).

Workup

  1. customTo a 20 mL microwave vial equipped with a stir bar
  2. customThe solution was capped
  3. customprecipitated out of solution
  4. filtrationThe white solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-30f64c8498c44086b11c1fb40326b828
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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