Potassium Hydroxide → [4-(Pyridin-2-ylmethoxy)-phenyl]-hydrazine dihydrochloride

HRID 2366086Notes

Reaction equation

HRID 2366086 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.[N:17]([O-])=O.[Na+].[O-]S(S([O-])=O)=O.[Na+].[Na+].[OH-].[K+]>O.CCOCC>[ClH:1].[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH2:17])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24489Sodium DithioniteHCID 23668193Sodium NitriteHCID 666020844-(Pyridin-2-ylmethoxy)-phenylamine hydrochloride

Product 1

HCID 44474905[4-(Pyridin-2-ylmethoxy)-phenyl]-hydrazine dihydrochlorideYield 129.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

4-(Pyridin-2-ylmethoxy)-phenylamine hydrochloride (95 g) was dissolved in water (1 L) at 0° C. and to this was added NaNO2 (26 g) in water (100 mL). The diazonium salt was allowed to form over 45 minutes and then it was poured slowly over 15 minutes into a rapidly stirred mixture of Na2S2O4 (350 g) in water (1 L) and ether (1 L) at 0° C. Stirring continued for 40 minutes then mixture was made basic using conc. KOH. After extraction using EtOAc (×2) the organic layers were washed with water, then brine, dried (MgSO4) and filtered. To this solution was added saturated HCl in EtOAc and a precipitated formed immediately. Collection of the solids by filtration followed by drying under vacuum provided the title compound as a tan solid (75 g).

Workup

  1. customto form over 45 minutes
  2. extractionAfter extraction
  3. washwere washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. filtrationfiltered
  6. additionTo this solution was added saturated HCl in EtOAc
  7. customa precipitated formed immediately
  8. customCollection of the solids
  9. filtrationby filtration
  10. customby drying under vacuum

Sources & evidence

ORD record
ord-d59cfd5b55524414b8f03adb7ffa783a
Source dataset
uspto-grants-2014_04
Patent number
US08697730B2

Reaction notes

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