Hydrochloric Acid → HCID 178524559, compound

HRID 514562Notes

Reaction equation

HRID 514562 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[N:10]([C:14]3[CH:19]=[C:18]([C:20]#N)[CH:17]=[CH:16][N:15]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-:22].[Na+].Cl.[OH2:25]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[N:10]([C:14]3[CH:19]=[C:18]([C:20]([OH:25])=[O:22])[CH:17]=[CH:16][N:15]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178510212HCID 178510212, compound

Product 1

HCID 178524559HCID 178524559, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 2-[3-(4-chlorophenyl)-5-hydroxypyrazol-1-yl]pyridine-4-carbonitrile (250 mg, 0.85 mmol) in EtOH (10 mL) and water (5 mL) was added NaOH (168 mg, 4.2 mmol) at r.t. The reaction mixture was stirred at 90° C. for 2 h. Removed EtOH, acidified with 1N HCl to pH 5, filtered, washed with ethyl acetate (5 mL) to give the title compound (200 mg, 75%) as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 6.20 (1H, s), 7.50 (2H, d, J=8.4 Hz), 7.76 (1H, d, J=4.0 Hz), 7.91 (2H, d, J=8.4 Hz), 8.26 (1H, s), 8.65 (1H, d, J=5.2 Hz), 12.20 (1H, brs), 13.96 (1H, brs). [M+H] Calc'd for C15H10ClN3O3, 316. Found, 316.

Workup

  1. filtrationfiltered
  2. washwashed with ethyl acetate (5 mL)

Sources & evidence

ORD record
ord-228514ec8a464e368545ea491146591e
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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