Nitric Acid → HCID 3520910, compound

HRID 1683150Notes

Reaction equation

HRID 1683150 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18](=[O:19])[C:7]=12.[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[C:12]3[CH:13]=[CH:14][C:15]([N+:1]([O-:4])=[O:2])=[CH:16][C:17]=3[C:18](=[O:19])[C:7]=12

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 72584Onychine

Product 1

HCID 3520910HCID 3520910, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of 35.2 ml of 98.9% strength sulfuric acid with 35.2 ml of 99% strength nitric acid was added dropwise at from +5° to 10° C. to a solution of 15.6 g (0.08 mol) of 4-methyl-5H-indeno[3,2-b]-pyridin-5-one in 35.2 ml of conc. sulfuric acid in the course of 1 hour. After stirring at 25° C. for 14 hours and additionally stirring at 70° C. for 4 hours, the mixture was cooled to 20° C., stirred into 500 g of ice and brought to pH 10 with a 50% strength aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate, the combined extracts were concentrated under reduced pressure and the residue was crystallized at +10° C. using 30 ml of ether. 13 g (67% of theory) of 4-methyl-7-nitro-5H- indeno[3,2-b]pyridin-5-one were obtained as yellow crystals of m.p. 225°-227° C.

Workup

  1. stirringadditionally stirring at 70° C. for 4 hours
  2. temperaturethe mixture was cooled to 20° C.
  3. extractionThe mixture was extracted with ethyl acetate
  4. concentrationthe combined extracts were concentrated under reduced pressure
  5. customthe residue was crystallized at +10° C.

Sources & evidence

ORD record
ord-7f4c48b6e1fa4a6a816c90e1d6dd4030
Source dataset
uspto-grants-1997_06
Patent number
US05637554

Reaction notes

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