Sodium Hydroxide → 3-Amino-5-bromopyridine-2-carbonitrile

HRID 968563Notes

Reaction equation

HRID 968563 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH-].[Na+]>Cl>[NH2:10][C:4]1[C:5]([C:8]#[N:9])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 220301763-Amino-5-bromopyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Mix 5-bromo-3-nitropyridine-2-carbonitrile (1.5 g, 5.3 mmol) and SnCl2-dihydrate (5.00 g, 26.3 mmol) in concentrated HCl and allow to stir at room temperature overnight. Work up by adding ice and carefully adding 10 M NaOH until basic. Extract twice with Et2O (200 mL), dry (Na2SO4) and evaporate. Purify by silica gel chromatography (75% hexane-EtOAc) to furnish 3-amino-5-bromopyridine-2-carbonitrile as a pale solid.

Workup

  1. additionby adding ice
  2. extractionExtract twice with Et2O (200 mL)
  3. dry with materialdry (Na2SO4)
  4. customevaporate
  5. customPurify by silica gel chromatography (75% hexane-EtOAc)

Sources & evidence

ORD record
ord-8b51a197813b44daa5c155df1e27b4bb
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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