Ammonium Hydroxide → 2-Amino-5-chloro-3-fluoropyridine
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]=1Participants
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
- customTo a 20 mL microwave vial equipped with a stir bar
- customThe solution was capped
- customprecipitated out of solution
- filtrationThe white solid was filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-30f64c8498c44086b11c1fb40326b828
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851484B2
Reaction notes
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