N-bromobutanimide → 2-Amino-5-bromo-4-chloropyridine

HRID 416696Notes

Reaction equation

HRID 416696 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O>C(#N)C>[Br:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 441818122-Amino-5-bromo-4-chloropyridineYield 80.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-amino-4-chloropyridine (0.50 g, 3.9 mmol) in acetonitrile (20 ml) was added dropwise a solution of N-bromosuccinimide (0.730 g, 4.1 mmol) in acetonitrile (10 ml). The reaction mixture was stirred at room temperature for 16 h then concentrated in vacuo. The crude product was purified by chromatography on silica gel (hexane/ethyl acetate 6:4) to give the title compound as a white solid (0.65 g, 80%); 1H-NMR (250 MHz, CDCl3) 6.63 (s, 1H) and 8.16 (s, 1H) (3-H, 6-H); LC-MS (ESI, m/z) Rt=4.8 min—206, 209 [(M+H+), BrCl isotopic pattern, 100%];

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude product was purified by chromatography on silica gel (hexane/ethyl acetate 6:4)

Sources & evidence

ORD record
ord-1559f527f0384364acc53e9a8de53c79
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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