Hydrochloric Acid → HCID 59161410, compound

To a solution of 2,5-difluoro-4-methylaminobenzonitrile (0.509 g, 3.03 mmol) in dry diethyl ether (40 ml) stirred at room temperature under nitrogen, was added dropwise by syringe diisobutylaluminium hydride (5.5 ml, 1.0 M in toluene, 5.5 mmol) and stirring continued for 16 h. The solution was chilled in an ice-bath and methanol (2.8 ml) was added dropwise and the mixture stirred for 1 h before 1.0 M HCl (17 ml) was added and stirring continued for a further 1 h. The reaction mixture was then partitioned between ether (50 ml) and water (50 ml) and the aqueous layer re-extracted with ether (50 ml). The combined ether extract was washed with 5% sodium bicarbonate solution (34 ml), then brine, dried (MgSO4) and evaporated to give a mixture of the desired aldehyde and unhydrolysed imine (0.511 g). The material was filtered through a plug of silica gel using 100% dichloromethane to give pure 2,5-difluoro-4-methylaminobenzaldehyde (x).

1. temperatureThe solution was chilled in an ice-bath
2. additionwas added
3. stirringstirring
4. waitcontinued for a further 1 h
5. customThe reaction mixture was then partitioned between ether (50 ml) and water (50 ml)
6. extractionthe aqueous layer re-extracted with ether (50 ml)
7. extractionThe combined ether extract
8. washwas washed with 5% sodium bicarbonate solution (34 ml)
9. dry with materialbrine, dried (MgSO4)
10. customevaporated
11. customto give
12. filtrationThe material was filtered through a plug of silica gel using 100% dichloromethane

ORD record

ord-b14f1ca7efcd4b7ab0053d9a29b69e19

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796277B2