1-(5-methyl-3-nitropyrazol-1-yl)propan-2-one → 1-(5-Methyl-3-nitro-pyrazol-1-yl)-propan-2-ol

HRID 2381405Notes

Reaction equation

HRID 2381405 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8](=[O:10])[CH3:9])[N:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[N:6]([CH2:7][CH:8]([OH:10])[CH3:9])[N:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

4

Reactant 2

HCID 9029141-(5-methyl-3-nitropyrazol-1-yl)propan-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 668753101-(5-Methyl-3-nitro-pyrazol-1-yl)-propan-2-olYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1-(5-methyl-3-nitro-pyrazol-1-yl)-propan-2-one (500 mg, 2.9 mmol) in ethanol (15 ml) was treated with sodium borohydride (111 mg, 0.29 mmol). The reaction was stirred at 25° C. for 2.5 h. At this time, the reaction was poured onto water and was extracted into ethyl acetate. The organics were concentrated in vacuo to afford 1-(5-methyl-3-nitro-pyrazol-1-yl)-propan-2-ol (440 mg, 88%) which was used without further purification; ES+-HRMS m/e calcd for C7H11N3O3 [M+H+] 186.0873, found 186.0873.

Workup

  1. additionAt this time, the reaction was poured onto water
  2. extractionwas extracted into ethyl acetate
  3. concentrationThe organics were concentrated in vacuo

Sources & evidence

ORD record
ord-978caf7941f34fe28f3b25897bc57690
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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