Sulfuric Acid → Ethyl 2-aminopyridine-4-carboxylate

HRID 1828450Notes

Reaction equation

HRID 1828450 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][N:13]=1)[C:8]([OH:10])=[O:9])(=O)C.CO[C:16]1C=CC(CN2N=NC(CC(OCC)=O)=N2)=C[CH:17]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(O)C>[NH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][N:13]=1)[C:8]([O:10][CH2:16][CH3:17])=[O:9]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 37744662-Acetamidopyridine-4-carboxylic acidHCID 15090418HCID 15090418, compound

Product 1

HCID 7015521Ethyl 2-aminopyridine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

2-(Acetylamino)isonicotinic acid (13 g, 73.60 mmol) synthesized by the method of Example 7, (A) was added with ethanol (50 ml) and toluene (150 ml) and heated to 100-110° C. The mixture was added dropwise with concentrated sulfuric acid (7 ml) and heated for 11 hour with stirring. The reaction solution was returned to room temperature and poured into saturated aqueous sodium hydrogencarbonate cooled with ice. The mixture was extracted with chloroform and the collected organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 7.6 g (23% for the two steps) of the title compound as pale yellow crystals without purification.

Workup

  1. temperatureheated for 11 hour
  2. customwas returned to room temperature
  3. temperaturecooled with ice
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialthe collected organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e38f909434c47afb977652a1747462d
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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