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

HRID 857918

반응식

HRID 857918 반응식
[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

참가 물질

5

반응물 2

HCID 219520821-Benzyl-5-nitro-1H-indazoleHCID 178418361HCID 178418361, 화합물2회

생성물 1

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

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d34f6227bcb24822a27c438fa8c750ba
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148220B2

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