1-(3-methoxypropyl)-6-nitro-1H-indazole → 1-(3-methoxypropyl)-1H-indazol-6-amine

HRID 660365Notes

Reaction equation

HRID 660365 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=2)[CH:8]=[N:7]1>CO.[Ni]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[CH:8]=[N:7]1

Participants

4

Reactant 1

HCID 596309911-(3-methoxypropyl)-6-nitro-1H-indazole

Product 1

HCID 596309741-(3-methoxypropyl)-1H-indazol-6-amineYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-(3-Methoxypropyl)-6-nitro-1H-indazole (33 g, 0.14 mol) was dissolved in methanol (400 mL) and Raney Ni (7 g) was added. The reaction mixture was hydrogenated under an atmosphere of hydrogen at rt for about 2 h. When the starting material has been consumed, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give 1-(3-methoxypropyl)-1H-indazol-6-amine (27 g, 94% yield) which was used in the next step without purification. 1H NMR (400 MHz, CDCl3): δ 7.84 (s, 1H), 7.51 (d, J=8.4 Hz, 1H), 6.73 (s, 1H), 6.67-6.65 (dd, J=6.8, 2.0 Hz, 1H), 4.36-4.33 (t, J=6.4 Hz, 2H), 4.30-3.80 (brs, 2H), 3.30 (s, 3H), 3.30-3.28 (m, 2H), 2.16-2.10 (m, 2H).

Workup

  1. customWhen the starting material has been consumed
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-707517d0abeb4a81928043055f4e9378
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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