4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole → 1-(Tetrahydro-2H-pyran-4-YL)-1H-pyrazol-4-amine

HRID 57775Notes

Reaction equation

HRID 57775 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=1)([O-])=O>CO.[Pd]>[O:12]1[CH2:11][CH2:10][CH:9]([N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 591862964-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole

Product 1

HCID 510637031-(Tetrahydro-2H-pyran-4-YL)-1H-pyrazol-4-amineYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole (568 mg, 2.88 mmol, 1 equiv) in methanol was circulated through a H-Cube® Continuous-flow hydrogenation reactor (ThalesNano) fitted with a palladium on carbon catalyst cartridge at 50° C. The collected solution was concentrated in vacuo to afford product as pink solid (458 mg, 95% yield). LCMS (ESI) m/z: 168.0.

Workup

  1. concentrationThe collected solution was concentrated in vacuo

Sources & evidence

ORD record
ord-70bae89315f14c35bf0aa6bb6e2e96bd
Source dataset
uspto-grants-2016_09
Patent number
US09434732B2

Reaction notes

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