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

HRID 1059618Notes

Reaction equation

HRID 1059618 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 86.9%

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%i 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-2c6f4d495cee421fb330a85e36b1281b
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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