Ammonia → HCID 19042735, compound

HRID 1683152Notes

Reaction equation

HRID 1683152 reaction equation
[C:1](O)(=O)[CH2:2]C.[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O.[CH3:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:31](=[O:32])[C:20]=12.N>O.S(=O)(=O)(O)O.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([C:23]1[N:22]=[C:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:31](=[O:32])[C:20]2=[C:19]([CH3:18])[CH:24]=1)[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 1032Propionic AcidHCID 62648Ammonium PersulfateHCID 72584Onychine

Product 1

HCID 19042735HCID 19042735, compoundYield 418%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

At 25° C., 3.6 g of silver nitrate (0.018 mol) and 26.4 g (0.3 mol) of propionic acid and, at 70° C. in the course of 40 minutes, a solution of 27.4 g (0.12 mol) of ammonium peroxodisulfate in 60 ml of water were added dropwise to a solution of 11.7 g (0.006 mol) of 4-methyl-5H-indeno[3,2-b]pyridin-5-one in 130 ml of 2N sulfuric acid. The mixture was stirred at 80° C. for a further 90 minutes, then cooled and rendered alkaline at about 10° C. with a 28% strength aqueous ammonia solution and extracted three times with methylene chloride, and the combined organic extracts were washed with 50 ml of water and concentrated. The residue was crystallized at 0° C. using 5 ml of diethyl ether. 5.6 g (41.8% of theory) of 2-ethyl-4-methyl-5H-indeno[3,2-b]pyridin-5-one were obtained as slightly yellow crystals of m.p. 68°-70° C.

Workup

  1. temperaturecooled
  2. customat about 10° C.
  3. extractionextracted three times with methylene chloride
  4. washthe combined organic extracts were washed with 50 ml of water
  5. concentrationconcentrated
  6. customThe residue was crystallized at 0° C.

Sources & evidence

ORD record
ord-d81dc16e8b9b449f9a4ebc17259254ae
Source dataset
uspto-grants-1997_06
Patent number
US05637554

Reaction notes

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