Sulfuric Acid → Methyl 2-amino-6-chloronicotinate

HRID 2079941Notes

Reaction equation

HRID 2079941 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

To methanol (50 mL) were added concentrated sulfuric acid (25 mL) and 2-amino-6-chloro-nicotinic acid (4.3 g, 25 mmol) described in Preparation Example A-1 (or A-4) on an ice bath, which was stirred at 70° C. for 5 hours. After cooling, an aqueous solution of sodium bicarbonate (90 g) was added to neutralize. The resulting solid was filtered to obtain the title compound (3.2 g, 17 mmol, 68%) as a light brown solid.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-c74a1e8aeec440cfa5b5beaeea791d02
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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