Chlorosuccinimide → Methyl 6-amino-5-bromo-3-chloropyridine-2-carboxylate

HRID 723525Notes

Reaction equation

HRID 723525 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[Br:12].[Cl:13]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([Cl:13])=[CH:4][C:3]=1[Br:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 10704661Methyl 6-amino-5-bromopicolinate

Product 1

HCID 21873807Methyl 6-amino-5-bromo-3-chloropyridine-2-carboxylateYield 95.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution methyl 6-amino-5-bromopyridine-2-carboxylate (20.04 g) in acetic acid (900 ml) was added N-chlorosuccinimide (13.96 g) and the resultant solution was heated to 120° C. for 1 hour. The solution was then evaporated and treated with excess aqueous sodium bicarbonate and extracted with dichloromethane. The organic fraction was dried and evaporated to give the product (21.98 g).

Workup

  1. customThe solution was then evaporated
  2. additiontreated with excess aqueous sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. customThe organic fraction was dried
  5. customevaporated

Sources & evidence

ORD record
ord-5939f59c7bb94a1cb073784e484478f9
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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