Nitric Acid → HCID 13278595, compound

HRID 1388670Notes

Reaction equation

HRID 1388670 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH2:10]([N:14]1[C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[N:22]=[CH:23][C:18]=2[C:17](=[O:30])[CH:16]=[CH:15]1)[CH2:11][CH2:12][CH3:13].[OH-].[NH4+]>O>[CH2:10]([N:14]1[C:19]2[N:20]=[C:21]([C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)[N:22]=[CH:23][C:18]=2[C:17](=[O:30])[C:16]([N+:6]([O-:9])=[O:7])=[CH:15]1)[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 14923Ammonium HydroxideHCID 460269HCID 460269, compound

Product 1

HCID 13278595HCID 13278595, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

C-8. 8-n-Butyl-6-nitro-2-(4-pyridinyl)pyrido[2,3-d]pyrimidin-5(8H)-one--To 7.2 g of concentrated sulfuric acid was added, with stirring and cooling keeping the temperature below 30° C., 10.8 ml of fuming sulfuric acid. To the resulting mixture was added 6.0 ml of fuming nitric acid with stirring, and cooling as necessary to keep the temperature below 30° C. To the stirred mixture of acids at room temperature was added 6.6 g of 8-n-butyl-2-(4-pyridinyl)pyrido[2,3-d]pyrimidin-5(8H)-one. The reaction mixture was heated with stirring, gradually raising the temperature to 90° over a twenty minute period and then maintaining the reaction mixture at 90°-95° C. for ten minutes. The reaction mixture was cooled to 30° C. and added to 500 ml of a mixture of ice and water. The resulting mixture was made basic by adding concentrated ammonium hydroxide and the resulting mixture was allowed to stand for one hour. The separated solid was collected, washed with water, dried at 65° C. in vacuo to produce 6.3 g of 8-n-butyl-6-nitro-2-(4-pyridinyl)pyrido[2,3-d]pyrimidin-5(8H)-one, m.p. 240°-241° C. The product was dissolved in 50 ml of boiling dimethylformamide, the solution treated with decolorizing charcoal and filtered, and the filtrate concentrated to a volume of about 30 ml and cooled to complete precipitation of the product. The product was collected, washed with a small quantity of cold ethanol, and dried at 65° C. in vacuo to produce 5.25 g of 8-n-butyl-6-nitro-2-(4-pyridinyl)pyrido[2,3-d]pyrimidin-5(8H)-one, m.p. 241°-243° C.

Workup

  1. temperaturecooling
  2. stirringwith stirring
  3. temperaturecooling as necessary
  4. customthe temperature below 30° C
  5. additionTo the stirred mixture of acids at room temperature
  6. temperatureThe reaction mixture was heated
  7. stirringwith stirring
  8. temperaturegradually raising the temperature to 90° over a twenty minute period
  9. temperaturemaintaining the reaction mixture at 90°-95° C. for ten minutes
  10. customThe separated solid was collected
  11. washwashed with water
  12. customdried at 65° C. in vacuo

Sources & evidence

ORD record
ord-d187eca5c5374b08bd5c342953754c9e
Source dataset
uspto-grants-1984_02
Patent number
US04432981

Reaction notes

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