Ethanol → Ethyl 6-Aminonicotinate

HRID 491381Notes

Reaction equation

HRID 491381 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH2:11](O)[CH3:12]>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:11][CH3:12])=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 184966-Aminonicotinic acid

Product 1

HCID 235927Ethyl 6-Aminonicotinate

Procedure

To a suspension of 1.3 g (9.4 mmol) 6-aminonicotinic acid in 100 mL of ethanol, was bubbled in dry hydrochloric acid at 0° C., then the solution was refluxed until all the solids dissolved. The solvents were removed under reduced pressure, the residue dissolved in ethyl acetate, washed with saturated sodium bicarbonate, brine and concentrated to afford 1.37 g of a white solid, m/e=166(M+H).

Workup

  1. customwas bubbled in dry hydrochloric acid at 0° C.
  2. temperaturethe solution was refluxed until all the solids
  3. dissolutiondissolved
  4. customThe solvents were removed under reduced pressure
  5. dissolutionthe residue dissolved in ethyl acetate
  6. washwashed with saturated sodium bicarbonate, brine
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bfd65f59cfeb455b9c09f7e993ca0679
Source dataset
uspto-grants-2009_05
Patent number
US07531538B2

Reaction notes

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