Ethanol → HCID 58137375, compound

HRID 1907819Notes

Reaction equation

HRID 1907819 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[N+:5]([O-:13])[C:6]([CH3:12])=[CH:7][C:8]=1[N+]([O-])=O.[O-:14][CH2:15][CH3:16].[Na+].O.[CH2:19](O)C>>[CH2:1]([O:2][C:3]1[N:4]=[N+:5]([O-:13])[C:6]([CH3:12])=[CH:7][C:8]=1[O:14][CH2:15][CH3:16])[CH3:19]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 2723922Sodium ethoxideHCID 64053053-methoxy-6-methyl-4-nitropyridazine 1-oxide

Product 1

HCID 58137375HCID 58137375, compound

Procedure

3-Methoxy-6-methyl-4-nitropyridazine 1-oxide (2 g) was initially charged in ethanol (100 ml) at RT. Thereafter, solid sodium ethoxide (1.4 g) was added in portions while stirring. After stirring at 55° C. for 1.5 h, the reaction mixture was cooled to RT and admixed with water, and the aqueous phase was extracted 3 times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was purified by means of preparative HPLC. The clean, product-containing fractions were combined, freed of the acetonitrile and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 176 mg of the desired product were obtained. The aqueous phase was freeze-dried to obtain 781 mg of the desired product. To obtain further product, the contaminated fractions from the chromatography were combined and freeze-dried. The residues were purified again by means of preparative HPLC, and the clean product was isolated as described above. A further 130 mg of product were obtained.

Workup

  1. stirringAfter stirring at 55° C. for 1.5 h
  2. extractionthe aqueous phase was extracted 3 times with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by means of preparative HPLC
  7. additionThe clean, product-containing fractions
  8. extractionextracted three times with dichloromethane
  9. dry with materialThe combined organic phases were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-771c215f88ac450ab6d5010a02cf645c
Source dataset
uspto-grants-2013_12
Patent number
US08598177B2

Reaction notes

Loading…