Hydrochloric Acid → HCID 86664083, compound

HRID 1615877Notes

Reaction equation

C(ON=O)(C)(C)C.C(#N)C.N[C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][C:13]=1[N+:29]([O-:31])=[O:30].[ClH:32]>C(OCC)(=O)C.[Cu](Cl)Cl>[Cl:32][C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][C:13]=1[N+:29]([O-:31])=[O:30]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of tert-butylnitrite (3.23 mL, 27.17 mmol), anhydrous copper(II) chloride (2.9 g, 21.74 mmol) and anhydrous acetonitrile (90 mL) was warmed to 70° C. Ethyl 3-(6-amino-5-nitropyridin-3-yl)benzoate (5.2 g, 18.11 mmol) was then added portionwise over a period 10 minutes to the reaction solution. The reaction mixture was maintained at 70° C. for 2 hours and then allowed to cool to room temperature. The reaction mixture was then poured into 110 mL of 20% aqueous HCl solution, followed by extraction with ethyl acetate. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography using a 95:5 v/v hexane:ethyl acetate as solvent to afford ethyl 3-(6-chloro-5-nitropyridin-3-yl)benzoate (3.4 g, 61% yield) as a tan solid.

Workup

temperatureto cool to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record: ord-357fd5b73e474e3484f9e1289251d59e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765747B2

Reaction notes

Loading…