Hydrazine hydrate (1:1) → HCID 12074214, compound

HRID 1369398Notes

Reaction equation

HRID 1369398 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH:7]=[CH:8][C:9]=1[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])=[O:11])([O-])=O.O.NN>CCO.C1COCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([N:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]2)[CH:7]=[CH:8][C:9]=1[S:10]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:11])=[O:12]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12074213HCID 12074213, compound

Product 1

HCID 12074214HCID 12074214, compoundYield 101.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[3-nitro-4-(phenylsulfonyl)phenyl]-1-piperazinecarboxylate (0.85 g, 1.8 mmol) in 20 mL of a 4:1 EtOH:THF solvent system is added Raney nickel (130 mg suspension in EtOH) followed by hydrazine monohydrate (0.44 mL, 9.1 mmol). The mixture is stired vigorously for 2 h and then filtered through celite that is pretreated with water. The filtrate is concentrated, and the residue crystallized from MeOH/EtOAc/hexane to give 0.76 g (99%) of the aniline as a white solid, mp 135-137° C.

Workup

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

Sources & evidence

ORD record
ord-a01f72c46c1e479396abb06d7302b468
Source dataset
uspto-grants-2003_06
Patent number
US06579870B2

Reaction notes

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