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

HRID 970381Notes

Reaction equation

HRID 970381 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 of 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-843bb1eecd8a453a8afee779bc9d9cff
Source dataset
uspto-grants-2007_12
Patent number
US07312212B2

Reaction notes

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