Sulfuric Acid → Methyl 2-amino-6-chloronicotinate

HRID 1927237Notes

Reaction equation

HRID 1927237 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 68.8%

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) described in Manufacturing Example 11-1 under ice cooling, which was stirred for 5 hours at 70° C. The reaction mixture was cooled to room temperature and then neutralized by adding an aqueous solution of sodium hydrogencarbonate (90 g) at the same temperature. The solids thus produced were filtered off to obtain the titled compound (3.2 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solids thus produced
  3. filtrationwere filtered off

Sources & evidence

ORD record
ord-5671af26fa90430492eb7ce25ebe0d0f
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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