Sodium Iodide → HCID 86668299, compound

HRID 75092Notes

Reaction equation

N[C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8].N([O-])=O.[Na+].[I-:18].[Na+].S(=O)(O)[O-].[Na+]>Cl.O.ClCCl>[Cl:8][C:7]1[CH:6]=[C:5]([Cl:9])[N:4]=[C:3]([C:10]([O:12][CH3:13])=[O:11])[C:2]=1[I:18]

Participants

Conditions

Temperature: 5 °C

Procedure

Methyl 3-amino-4,6-dichloropicolinate (1.2 g, 5.4 mmol) was dissolved in concentrated HCl (15 mL), cooled to 5° C., and treated with a solution of sodium nitrite (0.56 g, 8.1 mmol) in 2 ml of water. The reaction mixture was stirred for 20 minutes at 5° C. and then poured carefully into a rapidly stirred mixture of sodium iodide (3.8 g; 25 mmol) in 30 mL water and 30 mL of dichlormethane. After 30 minutes, a dilute solution of sodium bisulfite was added. The dichloromethane phase was separated and washed with water, washed with saturated sodium chloride, dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by flash chromatography (SiO2, hexane/ethyl acetate) to give the title compound as a tan solid (0.60 g, 33%): 82-83° C.; 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 4.00 (s, 3H); EIMS m/z 331.

Workup

waitAfter 30 minutes
customThe dichloromethane phase was separated
washwashed with water
washwashed with saturated sodium chloride
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
customThe crude product was purified by flash chromatography (SiO2, hexane/ethyl acetate)

Sources & evidence

ORD record: ord-3ef91e84ec6842c1af7b95eca0cdad76
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835409B2

Reaction notes

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