Water → (4-Bromo-3-methylphenyl)methanamine

HRID 586021Notes

Reaction equation

HRID 586021 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[CH3:16].O.[OH-].[Na+]>C(OCC)C>[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][C:9]=1[CH3:16]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27374944-Bromo-3-methylbenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 21756143(4-Bromo-3-methylphenyl)methanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

LiAlH4 (0.68 g) in diethyl ether (30 mL) was treated with 4-bromo-3-methylbenzonitrile (15 mmol) and refluxed for 2 hours. The mixture was cooled to 0° C. and treated in succession with water (0.7 mL), 20% NaOH (0.5 mL), and water (2.5 mL). The mixture was filtered through a celite pad and the filter cake was washed several times with diethyl ether. The filtrate was dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. MS (ESI+) m/z 194 (M+H)+; MS (ESI−) m/z 192 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 3.97 (s, 2H), 7.30 (m, 1H), 7.46 (m, 2H).

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe mixture was filtered through a celite pad
  3. washthe filter cake was washed several times with diethyl ether
  4. dry with materialThe filtrate was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3a98ecf6fad4454a6bac1fd9b305dc8
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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