Hydrazine hydrate (1:1) → HCID 12074222, compound

HRID 1369400Notes

Reaction equation

HRID 1369400 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH:7]=[CH:8][C:9]=1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O.O.NN>CCO.C1COCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([N:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]2)[CH:7]=[CH:8][C:9]=1[S:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12074221HCID 12074221, compound

Product 1

HCID 12074222HCID 12074222, compoundYield 102.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[3-nitro-4-(phenylsulfanyl)phenyl]-1-piperazinecarboxylate (1.7 g, 3.8 mmol) in 42 mL of a 4:1 EtOH:THF solvent system is added Raney nickel (260 mg suspension in EtOH) followed by hydrazine monohydrate (0.92 mL, 19 mmol). The mixture is stirred vigorously for 2 h and then filtered through celite that is pretreated with water. The filtrate is concentrated, the residue crystallized from MeOH/EtOAc/hexane to give 1.5 g (92%) of the aniline as a white foam.

Workup

  1. filtrationfiltered through celite that
  2. concentrationThe filtrate is concentrated
  3. customthe residue crystallized from MeOH/EtOAc/hexane

Sources & evidence

ORD record
ord-253d71c1f1964b35812139f76b29f568
Source dataset
uspto-grants-2003_06
Patent number
US06579870B2

Reaction notes

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