Ethanol → Ethyl 2-amino-5-methylnicotinate

HRID 1747844Notes

Reaction equation

HRID 1747844 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#N)=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-:17].[Na+].[Na+].O.[CH2:23]([OH:25])[CH3:24]>C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]([O:25][CH2:23][CH3:24])=[O:17])=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 130708422-Amino-5-methylpyridine-3-carbonitrile

Product 1

HCID 13070843Ethyl 2-amino-5-methylnicotinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-5-methylpyridine-3-carbonitrile (353 mg) in ethanol (10 mL) was added concentrated sulfuric acid (5 mL), and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was added dropwise to a mixture of sodium carbonate (10.6 g), water (50 mL) and ethyl acetate (50 mL) under ice-cooling with stirring. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (373 mg) as a colorless solid.

Workup

  1. temperaturecooling
  2. stirringwith stirring
  3. customThe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f7af0acb278e482b8806528288601b3b
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

Loading…