Sulfuric Acid → Methyl 2-amino-6-chloronicotinate

HRID 1690952Notes

Reaction equation

HRID 1690952 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[C:17](=O)([O-])O.[Na+]>CO>[CH3:17][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([Cl:16])=[N:15][C:7]=1[NH2:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 122639922-Amino-6-chloronicotinic acid

Product 1

HCID 57415887Methyl 2-amino-6-chloronicotinateYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Concentrated sulfuric acid (25 mL) and 2-amino-6-chloro-nicotinic acid (4.3 g, 25 mmol) described in Manufacturing Example 26-1-1 were added to methanol (50 mL) on an ice bath, and stirred at 70° C. for 5 hours. The reaction mixture was cooled and then neutralized by addition of aqueous sodium hydrogen carbonate (90 g) solution. The precipitated solids were filtered to obtain the title compound (3.2 g, 17 mmol, 68%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe precipitated solids were filtered

Sources & evidence

ORD record
ord-b0d036aa8c1242bdbc9606ffd895eed1
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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