Benzene → Morpholine, 4-(6-hydrazinyl-3-pyridazinyl)-, hydrochloride (1:2)

HRID 1065483Notes

Reaction equation

HRID 1065483 reaction equation
[N+](C1C=CC(C=[N:9][NH:10][C:11]2[N:12]=[N:13][C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:15][CH:16]=2)=CC=1)([O-])=O.C1C=CC=CC=1.C1(C)C=CC=CC=1.[Cl:38]CCl>C(Cl)(Cl)Cl>[ClH:38].[ClH:38].[O:20]1[CH2:21][CH2:22][N:17]([C:14]2[N:13]=[N:12][C:11]([NH:10][NH2:9])=[CH:16][CH:15]=2)[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 1140TolueneHCID 6344DichloromethaneHCID 70550960HCID 70550960, compound2×

Product 1

HCID 12603549Morpholine, 4-(6-hydrazinyl-3-pyridazinyl)-, hydrochloride (1:2)

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

One part by weight of the substituted benzylidenehydrazine (compounds of Examples 1 to 6) is heated together with 20 parts by volume of benzene (or toluene or dichloromethane or chloroform) and 20 parts by volume of concentrated hydrochloric (or 48% hydrobromic) acid while stirring at an internal temperature of 40° C. for 1 to 2 hours in such a way that the organic phase is replaced by fresh solvent every 30 minutes. After separation 80-90% of the substituted benzaldehyde can be recovered from the organic phase. From the acidic aqueous phase, 6-morpholino-3-pyridazinylhydrazine dihydrochloride (or dihydrobromide, respectively) is obtained after evaporation and triturating the residue with ethanol and ether.

Workup

  1. waitis replaced by fresh solvent every 30 minutes
  2. customAfter separation 80-90% of the substituted benzaldehyde
  3. customcan be recovered from the organic phase

Sources & evidence

ORD record
ord-d7f74f1af61c4b3091cbfcff9e9b89be
Source dataset
uspto-grants-1982_05
Patent number
US04329457

Reaction notes

Loading…