Ethanol → Ethyl 6-Aminonicotinate

HRID 724236Notes

Reaction equation

HRID 724236 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 is 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
  5. dissolutionthe residue dissolved in ethyl acetate
  6. washwashed with saturated sodium bicarbonate, brine
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf2c202b8eef48f58a6883fb8f999f3e
Source dataset
uspto-grants-2006_11
Patent number
US07141609B2

Reaction notes

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