Trifluoroacetic acid → 4-Aminonicotinic acid

HRID 50774

Reaction equation

HRID 50774 reaction equation
C(OC([NH:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 221726234-{[(Tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid

Product 1

HCID 3199794-Aminonicotinic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(N-t-butoxycarbonylamino)nicotinic acid (2.72 g, 11.4 mmol), TFA (10 mL), and CH2Cl2 (20 mL) is stirred at room temperature for 12 h. The volatiles are removed under reduced pressure, and the resulting crude 4-amino nicotinic acid is used directly in the next reaction.

Workup

  1. customThe volatiles are removed under reduced pressure
  2. customthe resulting crude 4-amino nicotinic acid is used directly in the next reaction

Sources & evidence

ORD record
ord-9e3cbd9745244c5e825a237891073967
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Linked notes

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