Acetic Acid → o-(Methylamino)phenol

Temperature

0 °C

1 g of benzoxazole was dissolved in 20 ml of THF. 0.9 g of NaBH4 were added under nitrogen and stirring. The suspension was cooled to 0° C. and 0.86 ml of acetic acid dissolved in 5 ml THF were slowly added, keeping the reaction temperature below 5° C. The reaction was stirred at 0° C. for 30 minutes and for further 12 hours at room temperature. The reaction mixture was again cooled to 0° C. and 50 ml of sat. NH4Cl solution were added carefully. The phases were separated and the aqueous layer extracted twice with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and filtered. Removal of the solvent afforded 0.97 g (of pure 2-(N-methylamino)-phenol.

1. additionwere slowly added
2. customthe reaction temperature below 5° C
3. stirringThe reaction was stirred at 0° C. for 30 minutes and for further 12 hours at room temperature
4. temperatureThe reaction mixture was again cooled to 0° C.
5. customThe phases were separated
6. extractionthe aqueous layer extracted twice with EtOAc
7. washThe combined organic layers were washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customRemoval of the solvent

ORD record

ord-eacbc67941af4de19ad9810b0d0cedc4

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846925B2