Sodium Carbonate → 5-Bromo-2-chloro-6-(N,N-dimethylamino)-4-methylpyridine-3-carboxamide

HRID 53542Notes

Reaction equation

HRID 53542 reaction equation
[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:12]#[N:13])[C:5]([Cl:11])=[N:6][C:7]=1[N:8]([CH3:10])[CH3:9].C(=O)([O-])[O-:16].[Na+].[Na+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:12]([NH2:13])=[O:16])[C:5]([Cl:11])=[N:6][C:7]=1[N:8]([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 199600285-bromo-2-chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridine

Product 1

HCID 199600805-Bromo-2-chloro-6-(N,N-dimethylamino)-4-methylpyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5-bromo-2-chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridine (1.3 g) in concentrated sulfuric acid (3 mL) was heated at 120° C. for 10 minutes. The mixture was cooled, diluted with water (50 mL), and neutralized with saturated sodium carbonate. After extraction with methylene chloride, evaporation of the organic phase gave 1.37 g of the title compound, suitable for use in the next reaction.

Workup

  1. temperatureThe mixture was cooled
  2. extractionAfter extraction
  3. customwith methylene chloride, evaporation of the organic phase

Sources & evidence

ORD record
ord-c19a768d91a2451cbbbb8117fdd94cca
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Reaction notes

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