Ethanol → HCID 178507862, compound

HRID 2397459Notes

Reaction equation

HRID 2397459 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8]C(OCC)=O)[N+:5]([O-:14])=[C:4]([NH:15]C(OCC)=O)[CH:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(O)C.[OH-].[K+]>O>[NH2:15][C:4]1[CH:3]=[C:2]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:7]=[C:6]([NH2:8])[N+:5]=1[O-:14]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 8083MorpholineHCID 14797Potassium HydroxideHCID 178473436HCID 178473436, compound

Product 1

HCID 178507862HCID 178507862, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-2,6-bis(ethoxycarbonylamino)pyridine 1-oxide (10.0 g., 0.03 mole) and 60 ml. of morpholine is refluxed with stirring under a nitrogen atmosphere for a period of 24 hrs. and concentrated to dryness. The residual material thus obtained is taken up in 200 ml. of absolute ethanol and 24.0 g. (0.36 mole) of 85% potassium hydroxide. After stirring at reflux temperature for a period of 16 hr., 200 ml. of absolute ethanol is added and reflux continued for an additional period of 30 hr. Concentration of the basic solution to dryness provides a residue which on stirring with water affords 4.4 g. (69% yield) of 2,6-diamino-4-(4-morpholinyl)pyridine 1-oxide as the free base, m.p. 315°-325° C. (dec.). The free base is taken up in absolute ethanol and acidified with ethanolic hydrogen chloride. Addition of ethyl acetate to the acidified ethanolic solution and cooling affords the product which is collected and crystallized from absolute ethanol to provide 2.8 g. of analytically pure 2,6-diamino-4-(4-morpholinyl)pyridine 1-oxide hydrochloride hydrate, m.p. 203.5°-206.5° C. (dec.) (corr.).

Workup

  1. concentrationand concentrated to dryness
  2. customThe residual material thus obtained
  3. stirringAfter stirring
  4. temperatureat reflux temperature for a period of 16 hr
  5. temperaturereflux
  6. waitcontinued for an additional period of 30 hr
  7. customConcentration of the basic solution to dryness provides a residue which
  8. customaffords 4.4 g

Sources & evidence

ORD record
ord-1ec65c740a2049b9a0ce36175ab32e0a
Source dataset
uspto-grants-1977_05
Patent number
US04021562

Reaction notes

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