Bromine → 6-Amino-5-bromopyridine-3-carbonitrile

HRID 1182051Notes

Reaction equation

HRID 1182051 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[Br:10]Br>CC(O)=O>[NH2:1][C:2]1[C:9]([Br:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 14912506-Amino-5-bromopyridine-3-carbonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 6-Amino-nicotinonitrile (102 mg, 0.86 mmol) in AcOH (2 mL) add a solution of Br2 1.0M in AcOH (0.86 mmol). Stir the mixture at room temperature for 2 hours. Eliminate the solvent. Purify by flash chromatography on silica gel (eluent: hexane/EtOAc 3/1) to afford the title compound (110 mg, 65%).

Workup

  1. customPurify by flash chromatography on silica gel (eluent: hexane/EtOAc 3/1)

Sources & evidence

ORD record
ord-ac0583a72f1347ac9f35ec47af184ec0
Source dataset
uspto-grants-2007_10
Patent number
US07288543B2

Reaction notes

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