Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86656156, compound

To a mixture of 1-bromo-2-naphthoic acid (1.04 g, 4.14 mmol, TCI America) and N,O-dimethylhydroxylamine hydrochloride (0.465 g, 4.76 mmol) in N,N-dimethylformamide (10 mL,) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.11 g, 4.76 mmol). After stirred at room temperature for 10 minutes, N,N-diisopropylethylamine (2.16 mL, 12.4 mmol) was added to the resulting mixture. The reaction was stirred at room temperature for 2 h, quenched with water, and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was concentrated and the residue was purified on silica gel, eluting with 0% to 50% ethyl acetate in hexane, to give the desired product (1.08 g, 88%). LCMS calculated for C13H13BrNO2(M+H)+: m/z=294.0; found: 294.2.

1. stirringThe reaction was stirred at room temperature for 2 h
2. customquenched with water
3. extractionextracted with EtOAc
4. washThe combined organic layers were washed with water, brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. concentrationThe residue was concentrated
8. customthe residue was purified on silica gel
9. washeluting with 0% to 50% ethyl acetate in hexane

ORD record

ord-55286a2ce1004101a1f12d08fb846661

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680108B2