Nitric Acid → HCID 12784293, compound

Temperature

80 °C

Alternatively, 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone is prepared step-wise starting with 1,2-dihydro-2-oxo-5-(4-pyridinyl)-nicotinonitrile as follows: A mixture containing 197 g. of 1,2-dihydro-2-oxo-5-(4-pyridinyl)-nicotinonitrile, 600 ml. of concentrated sulfuric acid and 150 liters of water was refluxed for twenty-four hours, cooled and poured into 10 liters of a mixture of ice and water. The mixture was neutralized with ammonium hydroxide and the separated precipitate was collected, washed with a small amount of cold water and dried in vacuo at 80° C. to yield 148 g. of 5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 258°-260° C. An 80 g. portion of 5-(4-pyridinyl)-2(1H)-pyridinone was added to 288 ml. of concentrated sulfuric acid and the mixture heated to 70° C. To this stirred solution kept at 70°-80° C. was added dropwise a mixture containing 102 ml. of 90% nitric acid and 29 ml. of concentrated sulfuric acid. The reaction mixture was heated at about 80° C. for three hours after addition of the mixture of acids. The reaction mixture was then cooled and poured into a mixture of ice and water with stirring. The precipitate was collected and dried. It was then slurried with water and neutralized with 10% aqueous potassium bicarbonate solution. The precipitate was collected, washed with water and dried in vacuo at 80° C. to yield 56 g. of 3-nitro-5-(4-pyridinyl)-2(1H)-pyridonone.

1. additionA mixture containing 197 g
2. temperaturecooled
3. customthe separated precipitate was collected
4. washwashed with a small amount of cold water
5. customdried in vacuo at 80° C.
6. customto yield 148 g
7. customkept at 70°-80° C.
8. additionwas added dropwise a mixture
9. additioncontaining 102 ml
10. additionafter addition of the mixture of acids
11. temperatureThe reaction mixture was then cooled
12. customThe precipitate was collected
13. customdried
14. customThe precipitate was collected
15. washwashed with water
16. customdried in vacuo at 80° C.
17. customto yield 56 g

ORD record

ord-6d4210a1a3514c8cb5307bf6831afe67

Source dataset

uspto-grants-1980_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04199586