Water → HCID 131711218, compound

HRID 1733065Notes

Reaction equation

HRID 1733065 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH3:9])C(=O)C2=CC=CC=C12.O.NN.O>C(O)C>[ClH:22].[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH:8]([CH3:9])[CH2:7][CH2:6][NH2:5])=[CH:11][CH:12]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 20302499HCID 20302499, compound

Product 1

HCID 131711218HCID 131711218, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

38.95 g of 1 -phthalimido-3-(4'-chloro-4-biphenylyl)-butane are boiled with 12.2 ml of 80% hydrazine hydrate in 400 ml of ethanol for 2 hours, while stirring, water is added, the mixture is cooled and the resulting 1-(3,4-dihydro-4-oxo-1-phthalazinyl-amino)-3-(4'-chloro-4-biphenylyl)-butane (m.p. 195°) is filtered off, dissolved in 450 ml of ethanol and 450 ml of 37% hydrochloric acid and boiled for 30 minutes, while stirring. The solution is concentrated and worked up using sodium hydroxide solution and ethyl acetate to give 3-(4'-chloro-4-biphenylyl)-butylamine. Hydrochloride, m.p. 256°-259°.

Workup

  1. temperaturethe mixture is cooled
  2. filtrationthe resulting 1-(3,4-dihydro-4-oxo-1-phthalazinyl-amino)-3-(4'-chloro-4-biphenylyl)-butane (m.p. 195°) is filtered off
  3. dissolutiondissolved in 450 ml of ethanol
  4. stirringwhile stirring
  5. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-8117e940cddd4046a21a98011f9ce195
Source dataset
uspto-grants-1980_12
Patent number
US04239759

Reaction notes

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