4-Nitroindazole → NoName_3327

HRID 887225Notes

Reaction equation

HRID 887225 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-])=O.[BH4-].[Na+]>C(O)C>[NH:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:4]([NH2:1])[C:5]=2[CH:6]=[N:7]1

Participants

4

Reactant 2

HCID 180574-NitroindazoleHCID 4311764Sodium borohydride

Product 1

HCID 413085NoName_3327Yield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Nitro-1H-indazole (1.63 g, 10 mmol) in ethanol (100 mL) was treated with BiCl3 (3.46 g, 11 mmol) followed by a portionwise addition of NaBH4. The reaction mixture was stirred at ambient temperature for 20 minutes and filtered through Celite. The filtrate was evaporated under reduced pressure and the residue was partitioned between ethyl acetate/dilute NaHCO3 solution. The organic layer was dried over MgSO4, filtered, and the filtrate concentrated under reduced pressure to provide the title compound as a tan solid (1.0 g). 1H NMR (300 MHz, DMSO-d6) δ 5.64 (s, 2H), 6.1 (d, 1H), 6.6 (d, 1H), 6.98 (t, 1H), 8.03 (s, 1H), 12.6 (s, 1H).

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate/dilute NaHCO3 solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-22bcdb50d5b6457ca8db3d85a1b0a681
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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