Hydrochloric Acid → 5-Fluoro-4-iodopyridin-3-amine

Reaction equation

[F:1][C:2]1[C:3]([I:15])=[C:4]([NH:8]C(=O)C(C)(C)C)[CH:5]=[N:6][CH:7]=1.Cl>>[F:1][C:2]1[C:3]([I:15])=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86726334N-(5-Fluoro-4-iodo-pyridin-3-yl)-2,2-dimethyl-propionamide

Product 1

HCID 867263335-Fluoro-4-iodopyridin-3-amineYield 83%

Procedure

N-(5-Fluoro-4-iodopyridin-3-yl)-2,2-dimethylpropanamide (8.46 g, 26.3 mmol) was heated at reflux in aqueous 3M HCl for 2 hours. The reaction was carefully quenched with aqueous sodium hydroxide (3M) until basic and the mixture was extracted with dichloromethane (×3). The combined organic fractions were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to afford the title compound (5.16 g, 21.7 mmol, 83% yield) as an off white solid, MS (ESI): m/z=239.18 (MH+), 90% pure by LCMS.

Workup

customThe reaction was carefully quenched with aqueous sodium hydroxide (3M) until basic and the mixture
extractionwas extracted with dichloromethane (×3)
dry with materialThe combined organic fractions were dried (MgSO4)
filtrationfiltered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-7cfc500a18bc4d429755eb360d611ac1
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315475B2

Reaction notes

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