Nicotinic Acid → 3-(Boc-amino)pyridine

HRID 1913700Notes

Reaction equation

HRID 1913700 reaction equation
C(O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:10]1([CH3:16])[CH:15]=CC=C[CH:11]=1.C([N:20](C(C)C)CC)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:43]([O:46]CC)(=[O:45])C>C(O)(C)(C)C>[C:10]([O:46][C:43]([NH:20][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:45])([CH3:16])([CH3:15])[CH3:11]

Participants

7

Reactant 5

HCID 938Nicotinic AcidHCID 1140TolueneHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 109323213-(Boc-amino)pyridine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a mixture of 3.69 g of nicotinic acid and 30 ml of toluene, 3.64 g of diisopropylethylamine, then 8.67 g of diphenylphosphoryl azide was added. The reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture, 4 ml of tert-butyl alcohol was added. The reaction mixture was stirred while heating at 80° C. for six hours. The reaction mixture was cooled to room temperature, then the reaction mixture was diluted with ethyl acetate, washed with water and then with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixture solvent of ethyl acetate and hexane to give 4.07 g of 3-(tert-butoxycarbonyl amino)pyridine.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperaturewhile heating at 80° C. for six hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed with water
  5. dry with materialwith a saturated sodium chloride solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with a mixture solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c9fbf8c34d854c35aed7b72c0d9d3b68
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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