Hydrazine hydrate (1:1) → n-(3-Aminophenyl)pyrrolidine-1-carboxamide

HRID 1852410Notes

Reaction equation

HRID 1852410 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.NN>CO.CCOC(C)=O.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 350596N-(3-nitrophenyl)pyrrolidine-1-carboxamide

Product 1

HCID 29798917n-(3-Aminophenyl)pyrrolidine-1-carboxamideYield 184.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Pyrrolidine-1-carboxylic acid (3-nitro-phenyl)-amide (850 mg, 3.40 mmol) was dissolved in 1:1 MeOH-EtOAc (100 mL). Raney®-Nickel was added (3 full spatulas) followed by hydrazine monohydrate (1.70 g, 34.0 mmol) over a 5 minute period. The reaction mixture was stirred at rt for 16 hours then filtered through celite, washing the precipitate with EtOAc (10×10 mL). The filtrate was evaporated in vacuo and the residue dissolved in EtOAc (50 mL). The solution was washed with saturated brine solution (2×50 mL), dried (Na2SO4), filtered, and the solvent evaporated in vacuo. The crude product was then purified by column chromatography (Flashmaster, 40-63 mesh silica gel, EtOAc→10% MeOH-EtOAc) to provide the title compound as a pale yellow solid (1.29 g, 92%); LC-MS, Rt=0.99 min (MeOH-FA), m/z 206 (MH+).

Workup

  1. filtrationthen filtered through celite
  2. washwashing the precipitate with EtOAc (10×10 mL)
  3. customThe filtrate was evaporated in vacuo
  4. dissolutionthe residue dissolved in EtOAc (50 mL)
  5. washThe solution was washed with saturated brine solution (2×50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. customThe crude product was then purified by column chromatography (Flashmaster, 40-63 mesh silica gel, EtOAc→10% MeOH-EtOAc)

Sources & evidence

ORD record
ord-4fb9fb2e7a314707ac63b07adfaacc58
Source dataset
uspto-grants-2015_02
Patent number
US08962609B2

Reaction notes

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