2-Amino-6-fluorobenzonitrile → 2-Amino-6-methoxybenzonitrile

A solution of 70 g (0.5 mol) of 2-amino-6-fluorobenzonitrile (prepared, e.g. according to U.S. Pat. No. 4,504,660) in 250 ml of N,N-dimethylformamide was prepared, and a solution of 30.6 g (0.55 mol) of sodium methoxide in 70 ml of methanol was added dropwise at room temperature while stirring. The mixture was then refluxed for 5 hours with stirring. The completion of the reaction was monitored by TLC. An additional 25 g of sodium methoxide in 35 ml methanol were added and the reaction mixture was refluxed for an additional 4 hours while stirring. The reaction mixture was concentrated under reduced pressure. The resulting residue was triturated with water, filtered off with suction and the solids obtained were dissolved in ethyl acetate. The resulting solution was concentrated in vacuo. The obtained residue was triturated with petroleum ether and filtered off with suction. Yield: 48 g (63% of theory) of a brownish solid having a melting point of 143-146° C.

1. temperatureThe mixture was then refluxed for 5 hours
2. stirringwith stirring
3. temperaturethe reaction mixture was refluxed for an additional 4 hours
4. stirringwhile stirring
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. customThe resulting residue was triturated with water
7. filtrationfiltered off with suction
8. customthe solids obtained
9. concentrationThe resulting solution was concentrated in vacuo
10. customThe obtained residue was triturated with petroleum ether
11. filtrationfiltered off with suction

ORD record

ord-17a227e2603a47b68c8952ab9b069445

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544637B2