Methanol → HCID 67248245, compound

HRID 2208916Notes

Reaction equation

HRID 2208916 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:10]=1[CH3:11])[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:17]O>>[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:10]=1[CH3:11])[C:7]([O:9][CH3:17])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 70606775-Amino-4-methyl-nicotinic acid

Product 1

HCID 67248245HCID 67248245, compoundYield 75%

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 5-amino-4-methylnicotinic acid (5.0 g, 32 mmol) in methanol (75 mL), was added conc. H2SO4 (5 mL) slowly at room temperature. The mixture was stirred at 70° C. for 12 h. On completion, the solvent was removed under reduced pressure and the residue was neutralized with saturated NaHCO3 solution. Extraction was carried out using EtOAc; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the title compound (4.1 g, 75%) which used without further purification.

Workup

  1. customOn completion, the solvent was removed under reduced pressure
  2. extractionExtraction
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f3f42014dcc4d8ca5894ca41a8cd248
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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