Hydrochloric Acid → HCID 86725517, compound

HRID 878547Notes

Reaction equation

HRID 878547 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[C:17]([C:19]#N)[CH:16]=[CH:15][N:14]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-:21].[Na+].Cl.C[OH:25]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[C:17]([C:19]([OH:25])=[O:21])[CH:16]=[CH:15][N:14]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86725516HCID 86725516, compound

Product 1

HCID 86725517HCID 86725517, compoundYield 87%

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[5-(4-bromophenyl)-1H-pyrazol-1-yl]pyridine-4-carbonitrile (100 mg, 0.31 mmol) in MeOH (4 mL) was added 10 N NaOH (4 mL), and the solution was heated under reflux conditions for 1 h. The solution was then cooled to 0° C. and the pH was adjusted to pH=2 by dropwise addition of 12 N HCl. The resulting precipitate was filtered to give the title compound (92 mg, 87%) as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 6.64 (1H, s), 7.16 (2H, d, J=8.8 Hz), 7.48 (2H, d, J=8.8 Hz), 7.79 (1H, s), 7.84 (1H, d, J=8.4 Hz), 8.13 (1H, s), 8.42 (1H, d, J=8.4 Hz). [M+H] Calc'd for C15H10BrN3O2, 344; Found, 344.

Workup

  1. temperaturethe solution was heated under reflux conditions for 1 h
  2. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-7edea14e9f764823b7ec723791fdfa6b
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

Loading…