Hydrochloric Acid → 2-chloro-4-(1H-pyrazol-3-yl)benzonitrile

Temperature

30 °C

2-Chloro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile (3.67 g; 12.75 mmol) was added to 8 ml of ethanol under nitrogen atmosphere. 15.5 ml of ˜10% HCl (g) in EtOH was slowly added and the temperature was raised to 30° C. where the mixture was stirred for 1 h. The temperature was then lowered to −10° C. and the mixture was again stirred for 30 min after which the product was precipitated as its HCl salt and was filtered and washed twice with 2 ml of ethanol. The product was dried in vacuo at +40° C. Yield 2.8 g. 2-Chloro-4-(1H-pyrazol-5-yl)benzonitrile hydrochloride (2.8 g; 11.47 mmol) was added to a mixture of 8 ml of water and 14 ml of MeOH under nitrogen atmosphere. To this 50% sodium hydroxide (1.5 ml; 28.7 mmol) was added keeping the temperature under 25° C. during the addition. The mixture was stirred for 2 h, the precipitate filtered and washed twice with 3 ml of lukewarm water. The product was dried in vacuo at +40° C. Yield 1.97 g. 1H-NMR (400 MHz; d6-DMSO): δ 6.99 (t, 1H), 7.89 (m, 1H), 7.99 (d, 2H), 8.15 (s, 1H), 13.27 (s, 1H).

1. customwas then lowered to −10° C.
2. stirringthe mixture was again stirred for 30 min after which the product
3. customwas precipitated as its HCl salt
4. filtrationwas filtered
5. washwashed twice with 2 ml of ethanol
6. customThe product was dried in vacuo at +40° C
7. customunder 25° C.
8. additionduring the addition
9. stirringThe mixture was stirred for 2 h
10. filtrationthe precipitate filtered
11. washwashed twice with 3 ml of lukewarm water
12. customThe product was dried in vacuo at +40° C

ORD record

ord-1c560cb223da47c78064922a5d2649b2

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975254B2