Methanol → 4-Phenoxy-2-pyridinemethanamine

HRID 2080044Notes

Reaction equation

HRID 2080044 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO.[Cl-].[NH4+]>O1CCCC1.O>[O:7]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][NH2:21])[CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23130778HCID 23130778, compound

Product 1

HCID 231304504-Phenoxy-2-pyridinemethanamineYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Next, to a solution of lithium aluminum hydride (725 mg, 19.1 mmol) in tetrahydrofuran (6.0 mL) was portionwise added a solution of the resulting 4-phenoxy-pyridine-2-carbonitrile (1.5 g, 7.65 mmol) in tetrahydrofuran (3 mL) on an ice bath, and the solution was stirred at room temperature for 15 hours. A mixture solvent of methanol and water (9:1) was added to the reaction solution, an aqueous solution of saturated ammonium chloride was further added, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, then, the solvent was evaporated to obtain the title compound (730 mg, 48%) as a pale brown oil. This was used in the next reaction without further purification.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1bb7d980371946e8a233d29f8ec17b72
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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