3-(Tert-butoxycarbonylamino)-2-methoxyisonicotinic acid → 3-Amino-2-methoxyisonicotinic acid

HRID 2422678

Reaction equation

HRID 2422678 reaction equation
C(OC([NH:8][C:9]1[C:17]([O:18][CH3:19])=[N:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][C:9]1[C:17]([O:18][CH3:19])=[N:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 672446053-(Tert-butoxycarbonylamino)-2-methoxyisonicotinic acid

Product 1

HCID 536346183-Amino-2-methoxyisonicotinic acidYield 56.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-[(T-butoxycarbonyl)amino]-2-methoxyisonicotinic acid (6.6 g, 24.6 mmol) was dissolved in trifluoroacetic acid (10 mL), and stirred at room temperature for 8 hours. The solvent was evaporated off under reduced pressure, and the resulting milky white solid was washed with water and ethanol to obtain a white solid (2.35 g, 56.8%). The mother liquid was again concentrated, and the resulting residue was washed with acetone and hexane to obtain a pale pink solid (1.3 g, 31.4%).

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. washthe resulting milky white solid was washed with water and ethanol

Sources & evidence

ORD record
ord-83d82c7eb4514d02a1dd8dfa59440ebb
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Linked notes

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