Sodium Hydroxide → 4-Amino-5-iodo-2-phenylpyridine

HRID 917458Notes

Reaction equation

[C:1]1([C:7]2[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[Na+].[I:19]Cl.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>C(O)(=O)C>[I:19][C:10]1[C:11]([NH2:13])=[CH:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=1

Participants

Conditions

Temperature: 15 °C

Procedure

To a stirred solution of 10.0 g (58.8 mmol) 2-phenyl-pyridin-4-ylamine in 300 ml glacial acetic acid was added 28.9 g (352 mmol) sodium acetate and the mixture was then cooled to 15° C. in an ice-bath and 19.1 g (118 mmol) iodine monochloride added in small portions (reaction slightly exothermic). The reaction mixture was stirred for 48 h at room temperature before being poured onto 500 ml 20% aq. sodium thiosulfate solution. The mixture was then made basic by addition of 5 N aq. sodium hydroxide solution and extracted three times with dichloromethane. The combined organic phases were washed with 20% aq. sodium thiosulfate solution, then dried over sodium sulfate and concentrated in vacuo. Flash chromatography (methanol/dichloromethane 3/97) followed by trituration in ether afforded 9.90 g (57%) 5-iodo-2-phenyl-pyridin-4-ylamine as an off-white solid. ES-MS m/e (%): 297 (M+H+, 100).

Workup

customreaction slightly exothermic)
extractionextracted three times with dichloromethane
washThe combined organic phases were washed with 20% aq. sodium thiosulfate solution
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b9e01318f9af4ee0ab671225981f4819
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273865B2

Reaction notes

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