3-(2-Methyl-1,3-dioxolan-2-yl)benzonitrile → [3-(2-Methyl-1,3-dioxolan-2-yl)phenyl]methanamine

HRID 2070993Notes

Reaction equation

HRID 2070993 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[O:12][CH2:11][CH2:10][O:9]1>CCOCC>[CH3:7][C:8]1([C:13]2[CH:14]=[C:15]([CH2:16][NH2:17])[CH:18]=[CH:19][CH:20]=2)[O:9][CH2:10][CH2:11][O:12]1

Participants

4

Reactant 2

HCID 105595463-(2-Methyl-1,3-dioxolan-2-yl)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 10726441[3-(2-Methyl-1,3-dioxolan-2-yl)phenyl]methanamineYield 57.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of LiAlH4 (114 mg, 3.6 mmol) in ether at 0° C. was added 3-(2-methyl-1,3-dioxolan-2-yl)benzonitrile (0.57 g, 3.0 mmol). The reaction mixture was stirred for 4 h and quenched with H2O (0.2 mL), 20% NaOH (0.2 mL), brine (0.6 mL). The resulting mixture was stirred for 1 h and filtered over celite and concentrated. The residue was purified by column chromatography (10% MeOH in CHCl3) to provide (3-(2-methyl-1,3-dioxolan-2-yl)phenyl)methanamine (334 mg, 57%).

Workup

  1. customquenched with H2O (0.2 mL), 20% NaOH (0.2 mL), brine (0.6 mL)
  2. stirringThe resulting mixture was stirred for 1 h
  3. filtrationfiltered over celite and
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (10% MeOH in CHCl3)

Sources & evidence

ORD record
ord-a245248bd5c74dfc95e89de2d190d76d
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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