Hydrazine hydrate (1:1) → HCID 54271296, compound

HRID 1415974Notes

Reaction equation

HRID 1415974 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=2[F:16])=[CH:4][N:3]=1.O.[NH2:18][NH2:19]>>[NH:18]([C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=2[F:16])=[CH:4][N:3]=1)[NH2:19]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19973430HCID 19973430, compound

Product 1

HCID 54271296HCID 54271296, compound

Procedure

An ethanolic solution of 2-chloro-5-(2-fluoro-5-methoxyphenyl) pyrazine and hydrazine monohydrate (10 equiv.) was refluxed under a N2 atmosphere for 6 h. The ethanol was removed under reduced pressure and the residue was partitioned between 5% HCl and CH2Cl2. The CH2Cl2 layer was extracted several times with 5% HCl and the combined aqueous portions were washed (1×) with CH2Cl2. The aqueous solution was made basic with 10N NaOH and then extracted (4×) with CH2Cl2. The combined CH2Cl2 portions were washed (1×) with brine, dried (Na2SO4), treated with decolorizing charcoal and filtered through celite. Evaporation of the solvent under reduced pressure yielded 2-hydrazino-5-(2-fluoro-5-methoxyphenyl)-pyrazine as a beige oil. ##STR38##

Workup

  1. customThe ethanol was removed under reduced pressure
  2. customthe residue was partitioned between 5% HCl and CH2Cl2
  3. extractionThe CH2Cl2 layer was extracted several times with 5% HCl
  4. washthe combined aqueous portions were washed (1×) with CH2Cl2
  5. extractionextracted (4×) with CH2Cl2
  6. washThe combined CH2Cl2 portions were washed (1×) with brine
  7. dry with materialdried (Na2SO4)
  8. additiontreated with decolorizing charcoal
  9. filtrationfiltered through celite
  10. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-baf34eedddc743bfbe68437735d7f414
Source dataset
uspto-grants-1999_06
Patent number
US05910590

Reaction notes

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