Cyclopropanecarbonyl chloride → N-(4-nitropyridin-2-yl)cyclopropanecarboxamide
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH2:10])[CH:5]=1)([O-:3])=[O:2].[CH:11]1([C:14](Cl)=[O:15])[CH2:13][CH2:12]1>N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:14]([CH:11]2[CH2:13][CH2:12]2)=[O:15])[CH:5]=1)([O-:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-nitropyridin-2-amine (Int-22, 32.4 g, 0.2096 mol) was dissolved in pyridine (200 mL). The reaction was cooled in an ice-water bath and cyclopropanecarbonyl chloride (28.5 mL, 0.314 mol) was added dropwise. Upon completing addition of the acid chloride, the reaction was stirred for 1 hr at 0° C. then warmed to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure and then diluted with water. Solids were collected by suction filtration. The filter cake was washed with water and hexanes. The isolated solids were then dried under vacuum to afford N-(4-nitropyridin-2-yl)cyclopropanecarboxamide (43.5 g, 100%). LCMS: (FA) ES+ 208; 1H NMR (300 MHz, CDCl3) δ ppm 8.90 (s, 1H), 8.50 (s, 1H), 8.50 (br s, 1H), 7.7 (dd, 1H), 1.6 (m, 1H), 1.2 (m, 2H), and 1.0 (m, 2H).
Workup
- temperatureThe reaction was cooled in an ice-water bath
- temperaturethen warmed to room temperature
- stirringstirred overnight
- concentrationThe reaction mixture was concentrated under reduced pressure
- additiondiluted with water
- filtrationSolids were collected by suction filtration
- washThe filter cake was washed with water and hexanes
- customThe isolated solids were then dried under vacuum
Sources & evidence
- ORD record
- ord-8dc518970c834e69896a791191103ceb
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513421B2
Reaction notes
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