Acetic Acid → HCID 15007192, compound

HRID 1085795Notes

Reaction equation

HRID 1085795 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([Br:10])=[C:6]([NH:11][CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[O:23][CH2:24][CH2:25][CH3:26])[C:5]([N+:27]([O-])=O)=[N:4]1)[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(O)(=O)C>C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([Br:10])=[C:6]([NH:11][CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[O:23][CH2:24][CH2:25][CH3:26])[C:5]([NH2:27])=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24489Sodium DithioniteHCID 15007230HCID 15007230, compound

Product 1

HCID 15007192HCID 15007192, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

530 mg of 2-ethyl-4-bromo-5-(2-n-propoxy-1- naphthylmethylamino)-6-nitro-3(2H)pyridazinone (Compound No. 48) was dissolved in a mixture comprising 50 ml of ethanol and 25 ml of a 10 wt% sodium carbonate aqueous solution. Then, 1.0 g of sodium hydrosulfite was gradually added under stirring, and the mixture was then stirred at room temperature for 2.5 hours. Glacial acetic acid was added to neutralize the reaction solution. Then, the solvent was distilled off under reduced pressure. Water was poured to the residue thus obtained, and the mixture was extracted with chloroform. The extract was washed sequentially with water and with a saturated sodium chloride aqueous solution and then dried over sodium sulfate. Then, the solvent was distilled off to obtain a residual yellowish orange solid substance. This product was purified by silica gel column chromatography by using chloroform and a mixture of chloroform/methanol (volume ratio of 10/1) as developers to obtain 10 mg of colorless crystals. This product was found to show the same behavior on the silica gel thin layer chromatography as the substance obtained in the above method (i), and was identical with it also in NMR, MS and IR spectrum.

Workup

  1. stirringthe mixture was then stirred at room temperature for 2.5 hours
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. additionWater was poured to the residue
  4. customthus obtained
  5. extractionthe mixture was extracted with chloroform
  6. washThe extract was washed sequentially with water and with a saturated sodium chloride aqueous solution
  7. dry with materialdried over sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customto obtain a residual yellowish orange solid substance
  10. customThis product was purified by silica gel column chromatography
  11. additiona mixture of chloroform/methanol (volume ratio of 10/1) as developers

Sources & evidence

ORD record
ord-e6d20346f3ac45dd801fc39ffaf22a6a
Source dataset
uspto-grants-1991_04
Patent number
US05011839

Reaction notes

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