Hydrochloric Acid → 3-Aminoisonicotinic acid

HRID 887708Notes

Reaction equation

HRID 887708 reaction equation
C(OC([NH:8][C:9]1[CH:17]=[N:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])=O)(C)(C)C.Cl>CO>[NH2:8][C:9]1[CH:17]=[N:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 212015233-(((Tert-butoxy)carbonyl)amino)pyridine-4-carboxylic acid

Product 1

HCID 4595313-Aminoisonicotinic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-tert-Butoxycarbonylamino-isonicotinic acid (450 mg) was dissolved in methanol (8 mL) and 6N hydrochloric acid (5 mL) was added to the solution. The resulting suspension was stirred under reflux for 2.5 hours, cooled to room temperature and washed 3× with chloroform. The aqueous layer was adjusted to pH-14 by addition of 2N sodium hydroxide solution, washed 3× with chloroform and adjusted again to pH-3 by addition of 2N hydrochloric acid. The aqueous layer was concentrated on a rotary evaporator to complete dryness and the residue was extracted with hot ethanol. The ethanol extract was filtered to remove insoluble material and concentrated in vacuum to afford 262 mg of the title compound of formula

Workup

  1. temperatureunder reflux for 2.5 hours
  2. washwashed 3× with chloroform
  3. additionThe aqueous layer was adjusted to pH-14 by addition of 2N sodium hydroxide solution
  4. washwashed 3× with chloroform
  5. additionadjusted again to pH-3 by addition of 2N hydrochloric acid
  6. concentrationThe aqueous layer was concentrated on a rotary evaporator
  7. extractionthe residue was extracted with hot ethanol
  8. extractionThe ethanol extract
  9. filtrationwas filtered
  10. customto remove insoluble material
  11. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-26eb1ca911a8441fb51fabb3027f12fc
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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