1-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-one → 1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol

HRID 62440

Reaction equation

HRID 62440 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[N:3]1.[BH4-].[Na+]>CCO>[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([OH:11])[C:5]=2[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 27657961-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-oneHCID 4311764Sodium borohydride

Product 1

HCID 138368981-methyl-4,5,6,7-tetrahydro-1H-indazol-4-olYield 68.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-methyl-6,7-dihydro-1H-indazol-4(5H)-one (1 g, 6.7 mmol) in EtOH (20 mL) was added NaBH4 (1.2 g, 33.3 mmol) in portions. The resulting mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure to afford the crude 1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (700 mg, 68.8%), which was used in the next step directly. MS-ESI (m/z): 153 (M+1)+ (Acq Method: 10-80AB_2 min_220 &254.1 cm; Rt: 0.17 min)

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c9ed543f7ed5432c8ce38d7841ae8fe8
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Linked notes

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