Ammonium Hydroxide → Ethyl 3-(6-phenyl-3-pyridazinyl)carbazate

HRID 372725

Reaction equation

HRID 372725 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([NH:14][NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[NH4+].[H][H]>[Pd].C(O)C>[C:5]1([C:8]2[N:13]=[N:12][C:11]([NH:14][NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 20326482Ethyl 3-[6-(p-bromophenyl)-3-pyridazinyl]carbazateHCID 178418361HCID 178418361, compound

Product 1

HCID 20326484Ethyl 3-(6-phenyl-3-pyridazinyl)carbazate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 15.57 g. of ethyl 3-[6-(p-bromophenyl)-3-pyridazinyl]carbazate, 1.5 g. of 10% palladium on carbon catalyst, 200 ml. of ethanol and 60 ml. of ammonium hydroxide is shaken under 40 lb. of hydrogen pressure for 4 hours with external heating of bottle by means of a heated jacket. The reaction mixture is filtered and the filtrate concentrated to a solid which is washed with water to give 10.1 g. of cream colored crystals. Recrystallization by dissolving in ethanol and diluting with petroleum ether gave white crystals, m.p. 158°-160° C.

Workup

  1. additionA mixture of 15.57 g
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate concentrated to a solid which
  4. washis washed with water
  5. customto give 10.1 g
  6. customRecrystallization
  7. dissolutionby dissolving in ethanol
  8. additiondiluting with petroleum ether
  9. customgave white crystals, m.p. 158°-160° C.

Sources & evidence

ORD record
ord-faea0a48b47b42c89a0bffe68740a93e
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Linked notes

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