N-bromobutanimide → 5-Bromo-2-tert-butylpyridin-4-amine

HRID 921034Notes

Reaction equation

HRID 921034 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=1)([CH3:12])([CH3:11])[CH3:10]>C(#N)C>[Br:1][C:16]1[CH:15]=[N:14][C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])=[CH:18][C:17]=1[NH2:19]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 8177532-(tert-Butyl)pyridin-4-amine

Product 1

HCID 679958335-Bromo-2-tert-butylpyridin-4-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Procedure analogous to V. Canibano et al., Synthesis 2001, 14, 2175. 18.7 g (105 mmol) of N-bromosuccinimide are added in portions at 40° C. to a vigorously stirred, light-protected solution of 15.0 g (100 mmol) of 2-tertbutyl-4-aminopyridine [39919-69-2] in 500 ml of acetonitrile, and the mixture is stirred for a further 30 h. The solvent is removed in vacuo, the residue is taken up in 500 ml of dichloromethane, washed five times with 500 ml of water each time and once with 300 ml of sat. sodium chloride solution, the organic phase is dried over sodium sulfate, and the solvent is then removed in vacuo. The crude product is recrystallised from cyclohexane. Yield: 17.9 g (78 mmol), 78%. Purity: >95% according to 1H-NMR.

Workup

  1. customCanibano et al., Synthesis 2001, 14, 2175
  2. customThe solvent is removed in vacuo
  3. washwashed five times with 500 ml of water each time
  4. dry with materialonce with 300 ml of sat. sodium chloride solution, the organic phase is dried over sodium sulfate
  5. customthe solvent is then removed in vacuo
  6. customThe crude product is recrystallised from cyclohexane

Sources & evidence

ORD record
ord-b754e70795634231ada8e1d6430e4e04
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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