Sulfuric Acid → Methyl 2-amino-6-chloronicotinate

HRID 1891566Notes

Reaction equation

HRID 1891566 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-chloronicotinic 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-1a1a2c3424d0421ea9b330217a610f44
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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