Ethanol → Ethyl 6-Aminonicotinate

HRID 2301320Notes

Reaction equation

HRID 2301320 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. temperature, then the 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-12bbeeeeeb514737a5b79230ee90663d
Source dataset
uspto-grants-2002_12
Patent number
US06500832B1

Reaction notes

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