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

HRID 64228Notes

Reaction equation

HRID 64228 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[O:6][CH2:5][CH2:4][O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>C1COCC1>[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]([CH2:10][NH2:11])[CH:12]=[CH:13][CH:14]=2)[O:3][CH2:4][CH2:5][O:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 105595463-(2-Methyl-1,3-dioxolan-2-yl)benzonitrileHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 10726441[3-(2-Methyl-1,3-dioxolan-2-yl)phenyl]methanamineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of cyano ketal 19 (290 mg, 1.53 mmol) in dry THF (10 mL) was cooled to 0° C. under a nitrogen atmosphere. Then a solution of 2 M lithium aluminum hydride (3 mmol) in THF was added over a 10-min period. The reaction mixture was stirred for 1.5 h and then ethyl acetate was added followed by slow addition of water to decompose the excess LAH. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in chloroform, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by column chromatography using chloroform and methanol as an eluent to give 20 (176 mg, yield 60%). 1H NMR (CDCl3, 400 MHz) δ 1.66 (s, 3H), 3.79 (t, J=6 Hz, 2H), 3.88 (s, 2H), 4.04 (t, J=6 Hz, 2H), 7.24-7.42 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-300d8fb7e3e7460a9bbfc0e1680736cc
Source dataset
uspto-grants-2016_09
Patent number
US09447134B2

Reaction notes

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