Sulfuric Acid → Methyl 2-amino-6-chloronicotinate

HRID 1171194Notes

Reaction equation

HRID 1171194 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 Production Example 4-1-1A (or 4-1-1B) were added to methanol (50 mL) while cooling with ice followed by stirring for 5 hours at 70° C. After allowing to cool on standing, the reaction mixture was neutralized with sodium bicarbonate (90 g). The resulting solid was filtered to obtain the title compound (3.2 g, 17 mmol, 68%) as a pale brown solid.

Workup

  1. temperaturewhile cooling with ice
  2. temperatureto cool
  3. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-6581dd3aa0854c6eb7511ee9df65db99
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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