2-Amino-4,6-dimethylpyridine → 5-Bromo-4,6-dimethylpyridin-2-amine

HRID 1846146Notes

Reaction equation

HRID 1846146 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Br:10]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:10])=[C:4]([CH3:9])[N:3]=1

Participants

4

Reactant 2

HCID 215072-Amino-4,6-dimethylpyridineHCID 67184N-bromobutanimide

Product 1

HCID 110308555-Bromo-4,6-dimethylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution containing 2.00 g (16.32 mmol) of 2-amino-4,6-dimethylpyridine in 25 mL of acetonitrile were added 2.90 g (16.32 mmol) of N-bromosuccinimide. The reaction mixture was stirred at room temperature under argon atmosphere for 5 h. The formed precipitate was filtered and dried to afford the expected product as a white solid: yield 2.76 g (84%). 1H-NMR (CDCl3) δ 6.22 (s, 1H), 4.39 (br, 2H), 2.48 (s, 3H), 2.25 (s, 3H); 13C-NMR (CDCl3) δ156.34, 155.23, 148.64, 112.26, 108.10, 25.10, 23.30.

Workup

  1. filtrationThe formed precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-46ce51ce51454eb9b112a43f2960df1c
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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