Water → N-Methylbiphenyl-2-amine

HRID 1351756Notes

Reaction equation

HRID 1351756 reaction equation
C(O[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:4][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 239257Ethyl [1,1'-biphenyl]-2-ylcarbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12246986N-Methylbiphenyl-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 18 g (0.075 mol) of 2-ethoxycarbonylaminobiphenyl in 100 ml of THF is added dropwise to a suspension of 14.2 g (0.373 mol) of lithium aluminum hydride in 300 ml of THF. The mixture is stirred for another 1 hour and then refluxed for 3 hours. Subsequently, while cooling in ice, 28 ml of water are firstly added dropwise and 18 ml of 15% strength aqueous sodium hydroxide are then added. After the precipitate has been separated off, it is washed a number of times with ether. The combined filtrates are dried over sodium sulfate, and the reddish liquid obtained after evaporation of the solvent is fractionated at 0.01 mbar. Bp.: 65–67° C. Yield: 10.64 g=77%.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureSubsequently, while cooling in ice
  3. customAfter the precipitate has been separated off
  4. washit is washed a number of times with ether
  5. dry with materialThe combined filtrates are dried over sodium sulfate
  6. customthe reddish liquid obtained
  7. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-5706791d3ad246f28d53dc8411bcc493
Source dataset
uspto-grants-2007_05
Patent number
US07217828B2

Reaction notes

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