Hydrochloric Acid → HCID 57635950, compound

To a solution of 1,5-dicyanopentane (1) (6.5 mL, 50 mmol) and ethyl formate (20 mL, 250 mmol) in dry diethyl ether (200 mL), sodium hydride (60%, 4 g. 100 mmol) was added. The re-action mixture was refluxed for four h, cooled to room temperature filtered and rinsed with ether and dried. To a solution of above obtained white solid in 80% ethanol/water was added hydrazine hydrochloride (6.29 g. 61 mmol). The reaction mixture was adjusted to pH 3 with concentrated HCl and then refluxed for 2 h, cooled to room temperature and neutralized with NaHCO3. Solvent was removed under reduced pressure and the residue was dried in vacuum. The residue was suspended in ethanol and filtered. The filtrate was concentrated, dissolved in 5% MeOH/CH2C12, filtered through a short silica gel column, rinsed with 5% MeOH/CH2C12 and concentrated to give 5-(5-amino-1H-pyrazol-4-yl)-pentanenitrile 2 as a oil.

1. temperatureThe re-action mixture was refluxed for four h
2. filtrationfiltered
3. washrinsed with ether
4. customdried
5. customTo a solution of above obtained white solid in 80% ethanol/water
6. temperaturerefluxed for 2 h
7. customSolvent was removed under reduced pressure
8. customthe residue was dried in vacuum
9. filtrationfiltered
10. concentrationThe filtrate was concentrated
11. dissolutiondissolved in 5% MeOH/CH2C12
12. filtrationfiltered through a short silica gel column
13. washrinsed with 5% MeOH/CH2C12
14. concentrationconcentrated

ORD record

ord-ed9066b057dc4a2984880261b01f3b6c

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517882B2