2,4-Difluorobenzonitrile → HCID 178513324, compound

Temperature

70 °C

To a mixture of 2,4-difluorobenzonitrile (1.39 g, 10 mmol) and DIEA (5.13 ml, 30 mmol) in EtOH (15 ml) was added 2.12 g of hydroxylamine hydrochloride (30 mmol) and the reaction was heated at 70° C. for 48 h. Half of the solvent was removed under reduced pressure. The mixture was poured in DCM (100 ml) and water (30 ml). 2.5 ml of NaOH 1N was added until pH=9-10. The organic layer was separated and the aqueous phase was extracted with DCM. The organic layers were combined, washed with water, dried over MgSO4, filtered and evaporated under reduced pressure to afford N-hydroxy-2,4-difluoro-benzamidine which was used without further purification for the next step.

1. customHalf of the solvent was removed under reduced pressure
2. additionThe mixture was poured in DCM (100 ml)
3. addition2.5 ml of NaOH 1N was added until pH=9-10
4. customThe organic layer was separated
5. extractionthe aqueous phase was extracted with DCM
6. washwashed with water
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customevaporated under reduced pressure

ORD record

ord-75a76bc526364ec1b1660d4618daf438

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834035B2