Methyl 4-((tert-butoxycarbonyl)amino)nicotinate → Methyl 4-aminopyridine-3-carboxylate

HRID 1787924Notes

Reaction equation

HRID 1787924 reaction equation
C([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]([O:17][CH3:18])=[O:16])(OC(C)(C)C)=O>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 1

HCID 23438729Methyl 4-((tert-butoxycarbonyl)amino)nicotinate

Product 1

HCID 592353Methyl 4-aminopyridine-3-carboxylateYield 92.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl 4-(Boc-amino)pyridine-3-carboxylate (2.38 g, 9.4 mmol) was dissolved in TFA (20 mL) and the solution was allowed to stir for 45 min. The solvent was removed in vacuo and the residue was partitioned between 25% isopropanol in chloroform and satd aq sodium bicarbonate. The layers were separated and the aqueous phase was extracted again with 25% isopropanol in chloroform. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give a solid which was washed with diisopropyl ether and dried in vacuo to give the title compound (1.327 g, 92%) as an off-white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between 25% isopropanol in chloroform
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted again with 25% isopropanol in chloroform
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a solid which
  9. washwas washed with diisopropyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-d0a6f6a08c924be985b821db55aa71fe
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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