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

HRID 1386200Notes

Reaction equation

HRID 1386200 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 NH40H, 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 NH40H

Sources & evidence

ORD record
ord-6ab618e6e09b432e95d4b4de4dcd0bb8
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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