Water → (4-Methoxypyridin-2-yl)methanamine

HRID 1784940Notes

Reaction equation

HRID 1784940 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:10])[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][NH2:10])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 134151564-Methoxypyridine-2-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 22292761(4-Methoxypyridin-2-yl)methanamineYield 38.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of 949 mg of 4-methoxypicolinonitrile in 15 mL of THF at 0° C. was added about 0.6 g of LiAlH4. The reaction became very exothermic. The mixture was allowed to warm to r.t. and after 40 min., the following were added in succession: 0.4 mL of H2O, 0.4 mL of 15% NaOH (aq.), and 1.2 mL of brine. The mixture was stirred at r.t. for 75 min. and then filtered through Celite and concentrated to give 377 mg of (4-methoxypyridin-2-yl)methanamine which was used for the next reaction without further purification.

Workup

  1. additionthe following were added in succession
  2. filtrationfiltered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6bd222f064324e87951b60d63ae9570d
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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