Hydrochloric Acid → Hydrazine, (4-chlorophenyl)methyl-

HRID 736281Notes

Reaction equation

HRID 736281 reaction equation
C(=[N:14][N:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH3:16])(C1C=CC=CC=1)C1C=CC=CC=1.Cl.[OH-].[Na+]>O1CCCC1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([N:15]([CH3:16])[NH2:14])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86620834N'-Benzhydrylidene-N-(4-chlorophenyl)-N-methylhydrazine

Product 1

HCID 11182748Hydrazine, (4-chlorophenyl)methyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N′-Benzhydrylidene-N-(4-chlorophenyl)-N-methylhydrazine (1.5 g, 4.68 mmol) is placed in 20 mL of tetrahydrofuran with stirring. 5 mL of 5 N hydrochloric acid are added thereto and the solution is then left stirring at a temperature in the region of 50° C. for 16 hours. The aqueous phase is then neutralized with 5 N sodium hydroxide and is then extracted with ethyl acetate. The oil obtained after extraction is purified by chromatography on silica gel, eluting at the start with an ethyl acetate/heptane mixture (10/90 by volume). N-(4-Chlorophenyl)-N-methylhydrazine is thus obtained in the form of a pale yellow oil, 0.53 g (72%). (Rf=0.48. 20/80 EtOAc/heptane (v/v)).

Workup

  1. waitthe solution is then left
  2. stirringstirring at a temperature in the region of 50° C. for 16 hours
  3. extractionis then extracted with ethyl acetate
  4. customThe oil obtained
  5. extractionafter extraction
  6. customis purified by chromatography on silica gel
  7. washeluting at the start with an ethyl acetate/heptane mixture (10/90 by volume)

Sources & evidence

ORD record
ord-6b5dc2cdbedf4be9a47534ca9532e3d1
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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