4-Nitrobenzaldehyde → Benzenemethanamine, 4-nitro-N-phenyl-

HRID 923384Notes

Reaction equation

HRID 923384 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)([O-:10])=[O:9].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO.C1(C)C=CC=CC=1>[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 6115AnilineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 96956Benzenemethanamine, 4-nitro-N-phenyl-Yield 59.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Combined aniline (6.16 g, 66.2 mmol) and 4-nitrobenzaldehyde (10.0 g, 66.2 mmol) in MeOH (165 mL) and toluene (165 mL), and heated to 60° C. for 3 h. Cooled the mixture to room temperature, added sodium borohydride (5.01 g, 132 mmol) portionwise, and then stirred at room temperature for 1 h. Added sat NaHCO3 and stirred for 1 h. Added water and extracted with EtOAc. Combined extracts were washed with brine, dried (MgSO4) filtered, and evaporated to an amber oil that was purified by chromatography on silica gel, eluting with CH2Cl2 to give the title compound (9.0 g, 59.6% yield).

Workup

  1. additionAdded
  2. stirringstirred for 1 h
  3. extractionAdded water and extracted with EtOAc
  4. washCombined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to an amber oil that
  8. customwas purified by chromatography on silica gel
  9. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-750157f6164245eb9402def8e65be9d0
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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