Hydrochloric Acid → 2-Chloro-5-fluoro-3-nitropyridine

HRID 1026536Notes

Reaction equation

HRID 1026536 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](N)=[N:6][CH:7]=1.N([O-])=O.[Na+].[OH-].[Na+].[ClH:18]>>[Cl:18][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([F:1])=[CH:7][N:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 217173395-Fluoro-3-nitropyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 107736262-Chloro-5-fluoro-3-nitropyridine

Conditions

Temperature
-15 °C

Procedure

5-Fluoro-3-nitropyridine-2-amine (2.66 g) suspended in concentrated hydrochloric acid (35 ml) was cooled to −15° C., and an aqueous solution (7 ml) of sodium nitrite (2.57 g) was added dropwise over 10 minutes. After stirring at −10° C. for 1 hour, and further stirring at room temperature for 1 hour, under ice cooling a 30% aqueous sodium hydroxide solution was added for neutralization. The insolubles were collected by filtration, washed with water, air-dried, and then redissolved in ethyl acetate, before the insolubles were filtered off. The filtrate was concentrated under reduced pressure to afford 2-chloro-5-fluoro-3-nitropyridine (1.41 g).

Workup

  1. additionwas added for neutralization
  2. filtrationThe insolubles were collected by filtration
  3. washwashed with water
  4. customair-dried
  5. dissolutionredissolved in ethyl acetate, before the insolubles
  6. filtrationwere filtered off
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8bd6472c514b4293b47f15c0e2484c3d
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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