Hydrogen Bromide → 6-Bromo-4-methylpyridin-2-amine

HRID 725751Notes

Reaction equation

HRID 725751 reaction equation
[C:1]([CH2:3][C:4]([CH3:9])(O)[CH2:5][C:6]#[N:7])#[N:2].[BrH:10]>C(O)(=O)C>[NH2:2][C:1]1[N:7]=[C:6]([Br:10])[CH:5]=[C:4]([CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 127207073-Hydroxy-3-methylpentanedinitrile

Product 1

HCID 221765076-Bromo-4-methylpyridin-2-amineYield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

56.4 g of 1,3-dicyano-2-methyl-2-hydroxypropane was added carefully to a 33% solution of hydrogen bromide in glacial acetic acid at ice-bath temperature. The reaction mixture was then stirred for 3 days at ambient temperature. The solvent was removed in vacuo and the residual oil was brought to pH 12 with a 10 molar aqueous solution of sodium hydroxide. This alkaline solution was extracted three times each with 100 ml ethyl acetate. The combined organic layers were dried with magnesium sulphate and the solvent removed in vacuo. 56 g (66%) of 6-amino-2-bromo-4-methylpyridine was obtained as a colourless solid of melting point 99° C.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThis alkaline solution was extracted three times each with 100 ml ethyl acetate
  3. dry with materialThe combined organic layers were dried with magnesium sulphate
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-632a4308ac39432e90cd94e0dae25135
Source dataset
uspto-grants-1998_01
Patent number
US05707933

Reaction notes

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