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

HRID 1852415
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1852415
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acid
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fb050feb02554d51be6b56241fb812d4
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08962598B2

Notizen zur Reaktion

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