Hydrazine hydrate (1:1) → prizidilol

HRID 1759363Notes

Reaction equation

HRID 1759363 reaction equation
[ClH:1].[Cl:2][C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH:17]([OH:24])[CH2:18][NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:7][CH:8]=1.O.[NH2:26][NH2:27]>ClCCl>[ClH:2].[ClH:1].[C:20]([NH:19][CH2:18][CH:17]([OH:24])[CH2:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[N:5]=[N:4][C:3]([NH:26][NH2:27])=[CH:8][CH:7]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 205319951-(tert-Butylamino)-3-[2-(6-chloropyridazin-3-yl)phenoxy]propan-2-ol--hydrogen chloride (1/1)

Product 1

HCID 71951prizidilol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 3-chloro-6-[2-(3-t-butylamino-2-hydroxypropoxy)phenyl]pyridazine hydrochloride (0.3 g.) and hydrazine hydrate (3 ml.) was heated under reflux for 50 minutes. After cooling, dichloromethane was added and this mixture was extracted with water, the dichloromethane was removed by evaporation and the residue was treated with a mixture of n-propanol (1.2 ml.) and concentrated hydrochloric acid (0.13 ml.) to give 3-[2-(3-t-butylamino-2-hydroxypropoxy)phenyl]-6-hydrazinopyridazine dihydrochloride, m.p. 163°-168°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 50 minutes
  3. temperatureAfter cooling
  4. extractionthis mixture was extracted with water
  5. customthe dichloromethane was removed by evaporation
  6. additionthe residue was treated with a mixture of n-propanol (1.2 ml.) and concentrated hydrochloric acid (0.13 ml.)

Sources & evidence

ORD record
ord-e358ac0dd3ca4f6da9971d4a2c31a36d
Source dataset
uspto-grants-1982_07
Patent number
US04340733

Reaction notes

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