Formamide, N-(1,1'-biphenyl)-4-yl- → 4-Biphenylamine, N-methyl-

HRID 1665679Notes

Reaction equation

HRID 1665679 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]([NH:13][CH:14]=O)=[CH:9][CH:8]=1>C1COCC1.C(OCC)(=O)C>[C:7]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:8]=[CH:9][C:10]([NH:13][CH3:14])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 95684Formamide, N-(1,1'-biphenyl)-4-yl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 1231884-Biphenylamine, N-methyl-Yield 92.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

LAH (96 mg, 2.5 mmol) was added portionwise to a cold (at 0° C.) solution of N-biphenyl-4-yl-formamide (100 mg, 0.5 mmol) in THF (2 mL) and the stirring was continued at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was quenched with 3% aq NaOH solution, the precipitate obtained was filtered, the filtrate was collected was concentrated under reduced pressure to get a residue. The residue was diluted with ethyl acetate, the organic layer was washed with brine solution and dried over sodium sulfate. The organic layer was concentrated under reduced pressure to afford 85 mg (91.39% Yield) of biphenyl-4-yl-methyl-amine.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with 3% aq NaOH solution
  3. customthe precipitate obtained
  4. filtrationwas filtered
  5. customthe filtrate was collected
  6. concentrationwas concentrated under reduced pressure
  7. customto get a residue
  8. washthe organic layer was washed with brine solution
  9. dry with materialdried over sodium sulfate
  10. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d1e4b563dbf24f99805fdff2f11b46cf
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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