Reaktion #1605773

Reaktionsgleichung

water

HCl

2-methoxy-4-methylbenzamide

Borane tetrahydrofuran

→

(2-methoxy-4-methylphenyl)methanamine

Ausbeute 64.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled to room temperature
2. 2
   Temperaturthe reaction mixture was then heated at 70° C. for 2 hrs
3. 3
   TemperaturAfter cooling
4. 4
   Waschenthe resulting solution was washed with ether
5. 5
   Sonstigewas basified with aq. NaOH (10 N) at 0° C. and saturated with K2CO3
6. 6
   Extraktionthen extracted with ethyl acetate
7. 7
   WaschenThe organic layer was washed with brine
8. 8
   Trocknendried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated

Vorschrift

To a solution of 2-methoxy-4-methylbenzamide (14.55 g, 88.08 mmol) in dry THF (50 mL) was added dropwise Borane-tetrahydrofuran complex (1.0 M in THF, 220 mL, 2.5 eq) at 0° C. under N2 atmosphere. The reaction mixture was then heated to 60° C. overnight. The reaction was cooled to room temperature, aq.HCl (6 N, 37 mL) was added carefully and the reaction mixture was then heated at 70° C. for 2 hrs. After cooling, water was added and the resulting solution was washed with ether. The aqueous layer was basified with aq. NaOH (10 N) at 0° C. and saturated with K2CO3 then extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated to give 8.5 g of (2-methoxy-4-methylphenyl)methanamine. (64% yield)

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