Trifluoroacetic acid → 5-Amino-2-chloro-isonicotinic acid

HRID 50825Notes

Reaction equation

HRID 50825 reaction equation
C(OC([NH:8][C:9]1[C:10]([C:16]([OH:18])=[O:17])=[CH:11][C:12]([Cl:15])=[N:13][CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C:9]1[C:10]([C:16]([OH:18])=[O:17])=[CH:11][C:12]([Cl:15])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 105641445-tert-Butoxycarbonylamino-2-chloroisonicotinic acid

Product 1

HCID 227367915-Amino-2-chloro-isonicotinic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid (1.91 g, 7 mmol) in CH2Cl2 (200 mL) is treated slowly with trifluoroacetic acid until homogeneous (ca. 12 mL). The solution is stirred overnight and extracted with dilute NH4OH, and the aqueous layer is then acidified with dilute HCl to gave a precipitate of 5-amino-2-chloropyridine-4-carboxylic acid (1.05 g, 87% yield). 1H NMR (DMSO) δ 9.01 (2H, m), 8.03 (1H, s), 7.48 (1H, s).

Workup

  1. extractionextracted with dilute NH4OH

Sources & evidence

ORD record
ord-25518bd1810147c3b75d570abaa7c84a
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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