Chlorine → Methyl-6-amino-5-chloro-2-methoxypyridine-3-carboxylate

HRID 1939245Notes

Reaction equation

HRID 1939245 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([O:12][CH3:13])=[N:7][C:8]([NH2:11])=[CH:9][CH:10]=1)=[O:4].[Cl:14]Cl>C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]([O:12][CH3:13])=[N:7][C:8]([NH2:11])=[C:9]([Cl:14])[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 11159681Methyl 6-amino-2-methoxynicotinate

Product 1

HCID 22101798Methyl-6-amino-5-chloro-2-methoxypyridine-3-carboxylateYield 67.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of methyl-6-amino-2-methoxypyridine-3-carboxylate (0.4 g) in acetic acid (10 ml) was treated with a solution of Cl2 (0.19 g) in HOAc (4 ml) at room temperature for 3 h. The AcOH was removed by rotary evaporation and the residue treated with aqueous NaHCO3 (50 mL) and the product extracted into EtOAc (100 mL). Evaporation afforded methyl-6-amino-5-chloro-2-methoxypyridine-3-carboxylate (0.32 g).

Workup

  1. customThe AcOH was removed by rotary evaporation
  2. additionthe residue treated with aqueous NaHCO3 (50 mL)
  3. extractionthe product extracted into EtOAc (100 mL)
  4. customEvaporation

Sources & evidence

ORD record
ord-8ee492bec8e14475aa6f0e1f353636af
Source dataset
uspto-grants-1997_12
Patent number
US05696129

Reaction notes

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