N-bromobutanimide → 3-Bromo-2-chloropyridin-4-amine

HRID 2422361Notes

Reaction equation

HRID 2422361 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.ClC1(N)C=CN=CC1.[Br:17]N1C(=O)CCC1=O>C(#N)C>[Br:17][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]=1[NH2:8].[Br:17][C:5]1[C:6]([NH2:8])=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 844322-Chloropyridin-4-amineHCID 67242974HCID 67242974, compound

Product 2

HCID 299193003-Bromo-2-chloropyridin-4-amineHCID 370300515-Bromo-2-chloropyridin-4-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-4-amino-pyridine was brominated according to the method described in Synthesis 2001, 14, 2175-2179: a solution of 4-chloro-4-amino-pyridine (12.3 g) in acetonitrile (500 ml) was treated with N-bromosuccinimide (17.8 g) and the resulting solution was stirred at room temperature for 24 hours. The solution was then concentrated in vacuo and the residue subjected to silica gel chromatography (cyclohexane:ethyl acetate 8:2) to afford 3-bromo-2-chloro-4-aminopyridine (12.2 g, m.p. 146° C. (hexane/ether)) and 5-bromo-2-chloro-4-aminopyridine (2.9 g, m. p. 117-119° C.).

Workup

  1. customdescribed in Synthesis 2001, 14, 2175-2179
  2. concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-2ae5aee330b1408cb65e9d31f5bf454d
Source dataset
uspto-grants-2011_06
Patent number
US07960401B2

Reaction notes

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