Hydrochloric Acid → 6-(Acetylamino)nicotinic acid

HRID 1787556Notes

Reaction equation

HRID 1787556 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12].C(OCC)(=O)C.Cl>N1C=CC=CC=1>[C:11]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 184966-Aminonicotinic acid

Product 1

HCID 4197446-(Acetylamino)nicotinic acidYield 26%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-aminonicotinic acid 5.00 g (36.5 mmol) and acetic anhydride 3.80 mL (40.2 mmol) in pyridine 30 mL was stirred at 140° C. for 24 hours. To the reaction mixture was added ethyl acetate and acidified with diluted HCl solution to pH 2. The organic layer was washed with water and brine, dried over MgSO4, filtrated and the solvent was evaporated. The residue was washed with diisopropyl ether to give the title compound 1.70 g as off-white solid. Yield 26%.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltrated
  4. customthe solvent was evaporated
  5. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-5308777b6f2a48389bc80056f7c09538
Source dataset
uspto-grants-2009_03
Patent number
US07511041B2

Reaction notes

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