Methanol → (6-Methyl-1H-indazol-5-yl)methylamine

HRID 2228739Notes

Reaction equation

HRID 2228739 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[C:11]#[N:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.[OH-].[Na+]>C1COCC1.O>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH2:11][NH2:12]

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 184708486-Methyl-1H-indazole-5-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 18470896(6-Methyl-1H-indazol-5-yl)methylamineYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-methyl-1H-indazole-5-carbonitrile (preparation 32) (230 mg, 1.47 mmol) in THF (10 ml) under nitrogen was treated with a solution of lithium aluminium hydride (1N, 3.66 ml, 3.66 mmol) in THF at 0° C. The resultant mixture was stirred for 16 hr warming to room temperature, then treated with MeOH (12 ml), H2O (0.8 ml), NaOH (4N, 2 ml) and H2O (4 ml). The resultant precipitate was removed by filtration, washed with THF and purified by chromatography (SiO2, eluting with 90:10:1 CH2Cl2:MeOH:NH3) to give the desired product (71 mg, 30%). 1H NMR (CD3OD) δ 2.40 (s, 3H), 3.95 (s, 2H), 7.35 (s, 1H), 7.70 (s, 1H), 7.95 (s, 1H), LRMS m/z=162.0 (M+1)+.

Workup

  1. customThe resultant precipitate was removed by filtration
  2. washwashed with THF
  3. custompurified by chromatography (SiO2, eluting with 90:10:1 CH2Cl2:MeOH:NH3)

Sources & evidence

ORD record
ord-45b5370c495249369462f7ed4b2f3d36
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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