Water → Methyl 4-amino-5,6-dichloro-2-pyridinecarboxylate

HRID 2407808Notes

Reaction equation

HRID 2407808 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.[Cl:13]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+].O>CN(C)C=O>[NH2:1][C:2]1[C:7]([Cl:13])=[C:6]([Cl:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 53485174Methyl 4-amino-6-chloropyridine-2-carboxylate

Product 1

HCID 58504072Methyl 4-amino-5,6-dichloro-2-pyridinecarboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The compound prepared in Example 404 (3.120 g) and N-chlorosuccinimide (2.456 g) were suspended in dimethyl formamide (100 mL) and stirred at 50° C. overnight. The reaction mixture was heated at 70° C. for a further 3 hours. The reaction mixture was added drop-wise to a stirred solution of 1:1 saturated aqueous sodium bicarbonate and water. The slurry was filtered and the solids dried under high vacuum to furnish the title compound (2.438 g), possessing the following physical data.

Workup

  1. temperatureThe reaction mixture was heated at 70° C. for a further 3 hours
  2. filtrationThe slurry was filtered
  3. customthe solids dried under high vacuum

Sources & evidence

ORD record
ord-93104871107f402da7d82396c220118d
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…