Tin dichloride dihydrate → 6-Cyclopropyl-5-phenylpyridin-3-amine

HRID 41990

Reaction equation

[CH:1]1([C:4]2[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][C:7]([N+:16]([O-])=O)=[CH:6][N:5]=2)[CH2:3][CH2:2]1.Cl[Sn]Cl.O>C(O)C>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([NH2:16])=[CH:8][C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-cyclopropyl-5-nitro-3-phenylpyridine (0.25 mmol, 0.06 g) and SnCl2.H2O (0.89 mmol, 0.2 g) in ethanol (2 ml) was heated at 80° C. for 1 hour. The solvent was evaporated and the crude residue was dissolved in water. The solution neutralised with 6N NaOH aqueous solution and extracted with dichloromethane. The solid residue was purified by chromatography over SiO2 eluting with dichloromethane/methanol mixtures affording 6-cyclopropyl-5-phenylpyridin-3-amine (0.03 g, 57% of yield) of the expected product.

Workup

customThe solvent was evaporated
dissolutionthe crude residue was dissolved in water
extractionextracted with dichloromethane
customThe solid residue was purified by chromatography over SiO2 eluting with dichloromethane/methanol

Sources & evidence

ORD record: ord-e2d2246eb6a34499a6fbd94959555ffd
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536165B2

Linked notes

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