1-Benzyl-5-nitro-1H-indazole → 1-(Phenylmethyl)-1H-indazol-5-amine

HRID 857918

Reaction equation

HRID 857918 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pt].C(O)C>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[N:9]=[CH:10]2

Participants

5

Reactant 2

HCID 219520821-Benzyl-5-nitro-1H-indazoleHCID 178418361HCID 178418361, compound2×

Product 1

HCID 2120691-(Phenylmethyl)-1H-indazol-5-amineYield 242.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A 500 mL Parr hydrogenator bottle was charged with 1-benzyl-5-nitroindazole (30.4 g, 120 mmol), absolute ethanol (240 mL) and 5% platinum on carbon (1.5 g, 50% wet). The bottle was placed on a Parr hydrogenation apparatus, the bottle pressurized with hydrogen to 50 psi and the bottle shook until the uptake of hydrogen ceased. The contents of the bottle were then transferred to a 1 L round bottomed flask, warmed to approximately 60° C. under nitrogen and rapidly filtered through a celite pad. The filter cake was washed with ethanol (100 mL). Water (250 mL) was then added to the filtrate and the resulting suspension stirred for 4 hours in an ice bath. The resulting solids were isolated by filtration, and the solids dried on the pump for 1 h. Three additional reduction runs were carried out under identical conditions. The four separate batches of material were then combined to give 87.4 g of crude material, which was re-crystallized from ethyl acetate (900 mL). Filtration and drying under reduced pressure (1 mmHg) afforded 65.0 g (59%) of the title compound as a light yellow solid.

Workup

  1. customThe contents of the bottle were then transferred to a 1 L round bottomed flask
  2. filtrationrapidly filtered through a celite pad
  3. washThe filter cake was washed with ethanol (100 mL)
  4. additionWater (250 mL) was then added to the filtrate
  5. customThe resulting solids were isolated by filtration
  6. customthe solids dried on the pump for 1 h
  7. customThe four separate batches of material
  8. customto give 87.4 g of crude material, which
  9. customwas re-crystallized from ethyl acetate (900 mL)
  10. filtrationFiltration
  11. customdrying under reduced pressure (1 mmHg)

Sources & evidence

ORD record
ord-d34f6227bcb24822a27c438fa8c750ba
Source dataset
uspto-grants-2006_12
Patent number
US07148220B2

Linked notes

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