Methanol → 4-[1-(3-Amino-pyrazol-1-yl)-butyl]-benzoic acid methyl ester

HRID 546102Notes

Reaction equation

HRID 546102 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:14]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[N:15]2)[CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=1.CO.NN>C(OCC)(=O)C.[Ni].O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:5]=[CH:6][C:7]([CH:10]([N:14]2[CH:18]=[CH:17][C:16]([NH2:19])=[N:15]2)[CH2:11][CH2:12][CH3:13])=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 67188885HCID 67188885, compound

Product 1

HCID 671891404-[1-(3-Amino-pyrazol-1-yl)-butyl]-benzoic acid methyl esterYield 94.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 4-[1-(3-nitro-pyrazol-1-yl)-butyl]-benzoic acid methyl ester (127 mg, 0.42 mmol) was dissolved in ethyl acetate (3 mL) and methanol (3 mL) was added. While stirring, a 50% slurry of raney nickel in water (500 μL) was added followed by hydrazine (150 μL). Immediate effervescence was observed. The reaction continued to stir and bubble for 30 min. The reaction was passed through a plug of celite and concentrated in vacuo to afford 4-[1-(3-amino-pyrazol-1-yl)-butyl]-benzoic acid methyl ester (108 mg, 94%) as a clear oil: ESI-LRMS m/e calcd for C15H19N3O2 [M+] 273.15, found 274.29 [M+H+], 547.43 [2M+H+].

Workup

  1. stirringto stir
  2. custombubble for 30 min
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1aa66a301824c29b9cebee706986221
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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