Hydrochloric Acid → HCID 69023914, compound

HRID 1865134Notes

Reaction equation

HRID 1865134 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:27])[N:8]=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]#[N:24])=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Na+].Cl>CCO>[C:25]([C:9]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)=[C:6]([C:4]([OH:5])=[O:3])[N:7]([CH3:27])[N:8]=1)#[N:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69019446HCID 69019446, compound

Product 1

HCID 69023914HCID 69023914, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve the 5-cyano-4-(2′-cyano-biphenyl-4-yl)-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (37 mg, 0.10 mmol, prepared in example Pz-2) in 2 mL of EtOH, add 1 mL of 2N aqueous NaOH and heat to reflux. After 20 minutes cool the reaction mixture in an ice-bath and add 2 mL of 1N aqueous HCl. Stir 10 minutes and filter, rinsing with 1 mL of EtOH followed by 2 mL of water. Vacuum-dry at 50° C. overnight to give the title compound. Yield=7.0 mg (21%). MS(ES−, m/e)=283 (M+−COOH).

Workup

  1. temperatureheat to reflux
  2. temperatureAfter 20 minutes cool the reaction mixture in an ice-bath
  3. filtrationfilter
  4. washrinsing with 1 mL of EtOH
  5. customVacuum-dry at 50° C. overnight

Sources & evidence

ORD record
ord-88c566d6f0904baf91e2e4698edcab43
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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