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

HRID 2256164Notes

Reaction equation

HRID 2256164 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-3a4ca13718734fbea5a8bb3a77dd0458
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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