Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 17981728, compound

Temperature

3.5 °C

Cool a mixture of N-methyl-O-methyl hydroxylamine hydrochloride (118 mmol) and toluene (125 mL) to −5° C. Slowly add trimethylaluminum (2 M in heptane, 59.2 mL, 118 mmol) to the mixture over 20 minutes, maintaining the reaction temperature from −1 to 8° C. After about 5 minutes slowly warm the mixture to room temperature and stir for 1.5 hours. Add a solution of methyl p-fluoromandelate (11.1 g, 60 mmol) in 75 mL of toluene over 30 min without external cooling. Cool the reaction to 0° C. and quench with 10% hydrochloric acid. Extract with ethyl acetate (4×250 mL). Wash the combined ethyl acetate layers sequentially with water and saturated aqueous sodium chloride, dry over sodium sulfate and concentrate under reduced pressure to provide 12.1 g (82%) of the desired compound.

1. temperatureCool
2. temperatureAfter about 5 minutes slowly warm the mixture to room temperature
3. temperatureCool
4. customthe reaction to 0° C.
5. customquench with 10% hydrochloric acid
6. extractionExtract with ethyl acetate (4×250 mL)
7. washWash the combined ethyl acetate layers sequentially with water and saturated aqueous sodium chloride
8. dry with materialdry over sodium sulfate
9. concentrationconcentrate under reduced pressure

ORD record

ord-6d7ff9fae2484e7d95f86516a34fdf0d

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07320995B2