N-bromobutanimide → 5-Bromo-6-ethylpyridin-2-amine

HRID 1049244Notes

Reaction equation

HRID 1049244 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[N:3]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)Cl>[Br:17][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][C:4]=1[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 890216-Ethylpyridin-2-amine

Product 1

HCID 217103385-Bromo-6-ethylpyridin-2-amineYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 0° C. solution of 2-amino-6-ethylpyridine (3.00 g, 24.56 mmol) in CHCl3 (25 mL) was treated portion-wise with NBS (4.37 g, 24.56 mmol) over 30 minutes, stirred for 45 minutes, then concentrated to dryness. The residue was treated with EtOAc, the solids removed via filtration and the filtrate concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 5-bromo-6-ethylpyridin-2-amine (3.83 g, 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.42 (d, J=8.6 Hz, 1H), 6.20 (d, J=8.7 Hz, 1H), 6.03 (s, 2H), 2.60 (q, J=7.5 Hz, 2H), 1.10 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 203.0 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue was treated with EtOAc
  3. customthe solids removed via filtration
  4. concentrationthe filtrate concentrated to dryness
  5. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-5ff8f0c6deda4ef9aac432c99d8c3a82
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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