Ethanol → Ethyl 6-Aminonicotinate

HRID 886642Notes

Reaction equation

HRID 886642 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-d6f9e670a411414ea7114ea8411633d4
Source dataset
uspto-grants-2012_08
Patent number
USRE043596E1

Reaction notes

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