Aniline → N-(2,4-dimethoxybenzyl)aniline

HRID 1852415Notes

Reaction equation

HRID 1852415 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(C)C=CC=CC=1.O.[BH4-].[Na+]>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 691752,4-DimethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 22272177Toluene water

Product 1

HCID 775299N-(2,4-dimethoxybenzyl)aniline

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 1140TolueneSolvent

Procedure

Trifluoroaceticacid (10 drops) was added to a solution of 2,4-dimethoxybenzaldehyde (16.62 g, 100 mmol) and aniline (9.31 g, 100 mmol) in toluene (100 mL). The reaction mixture was stirred at reflux temperature and toluene/water was distilled off during 1.5 h. After cooling the reaction mixture was concentrated at reduced pressure and the residue was dissolved in MeOH (200 mL). NaBH4 (2.0 g, 54 mmol) was added in portions during 20 min and the reaction mixture was then stirred for 1 h. The product (22.16 g, 91%) crystallized from the reaction mixture and was isolated by filtration.

Workup

  1. distillationwas distilled off during 1.5 h
  2. temperatureAfter cooling the reaction mixture
  3. concentrationwas concentrated at reduced pressure
  4. dissolutionthe residue was dissolved in MeOH (200 mL)
  5. stirringthe reaction mixture was then stirred for 1 h
  6. customThe product (22.16 g, 91%) crystallized from the reaction mixture
  7. customwas isolated by filtration

Sources & evidence

ORD record
ord-fb050feb02554d51be6b56241fb812d4
Source dataset
uspto-grants-2015_02
Patent number
US08962598B2

Reaction notes

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