Trifluoroacetic acid → 5-Amino-2-fluoroisonicotinic acid

HRID 1281963Notes

Reaction equation

HRID 1281963 reaction equation
C(OC([NH:8][C:9]1[C:10]([C:16]([OH:18])=[O:17])=[CH:11][C:12]([F:15])=[N:13][CH:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[NH2:8][C:9]1[C:10]([C:16]([OH:18])=[O:17])=[CH:11][C:12]([F:15])=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 106110655-((tert-Butoxycarbonyl)amino)-2-fluoroisonicotinic acid

Product 1

HCID 27625115-Amino-2-fluoroisonicotinic acidYield 75.6%

Procedure

Reaction of 5-[N-(tert-butoxycarbonyl)amino]-2-fluoropyridine-4-carboxylic acid (1.0 g, 3.9 mmol) with TFA as described above gives 5-amino-2-fluoropyridine-4-carboxylic acid(0.46 g, 74%). 1H NMR (DMSO) δ 7.85 (1H, d, J=1.5 Hz), 7.23 (1H, d, J=2.5 Hz).

Sources & evidence

ORD record
ord-e7eea88c1c744cffa3307a5c890d3652
Source dataset
uspto-grants-2002_09
Patent number
US06455534B2

Reaction notes

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