Methanol → 4-(3-amino-1H-pyrazol-1-yl)butan-1-ol

HRID 546086Notes

Reaction equation

HRID 546086 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C:10]#[C:11][CH2:12][OH:13])[N:5]=1)([O-])=O.CO.NN>C(OCC)(=O)C.[Ni].O>[NH2:1][C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[N:5]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 671932964-(3-Nitro-pyrazol-1-yl)-but-2-yn-1-ol

Product 1

HCID 204512994-(3-amino-1H-pyrazol-1-yl)butan-1-olYield 98%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 4-(3-nitro-pyrazol-1-yl)-but-2-yn-1-ol (prepared in example 52, 113 mg, 0.62 mmol) was dissolved in ethyl acetate (3 mL) and methanol (3 mL) was added. While stirring, a 50% slurry of raney nickel in water (1.3 mL) was added followed by hydrazine (400 μL). Immediate effervescence was observed. The reaction continued to stir and bubble for 25 min. The reaction was passed through a plug of celite and concentrated in vacuo to afford 4-(3-amino-pyrazol-1-yl)-butan-1-ol (93 mg, 98%) as a clear oil: ESI-LRMS m/e calcd for C7H13N3O [M+] 155.11, found 156.32 [M+H+].

Workup

  1. stirringto stir
  2. custombubble for 25 min
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8148d61361804ced87872c86395c433e
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

Loading…