Ethanol → 2-(3-Cyano-4-phenylpyrrole-1-yl)-5-hydroxyisonicotinic acid

HRID 570856Notes

Reaction equation

HRID 570856 reaction equation
C([O:3][C:4](=[O:25])[C:5]1[C:10]([OH:11])=[CH:9][N:8]=[C:7]([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([C:23]#[N:24])=[CH:13]2)[CH:6]=1)C.O1CCCC1.C(O)C.[OH-].[Li+]>O>[C:23]([C:14]1[C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:16][N:12]([C:7]2[CH:6]=[C:5]([C:10]([OH:11])=[CH:9][N:8]=2)[C:4]([OH:25])=[O:3])[CH:13]=1)#[N:24]

Participants

6

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 594778862-(3-Cyano-4-phenylpyrrole-1-yl)-5-hydroxyisonicotinic acid ethyl ester

Product 1

HCID 594775592-(3-Cyano-4-phenylpyrrole-1-yl)-5-hydroxyisonicotinic acidYield 65.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(3-cyano-4-phenylpyrrole-1-yl)-5-hydroxyisonicotinic acid ethyl ester (0.050 g) in a mixed solvent of tetrahydrofuran (3.6 mL) and ethanol (1.2 mL) was added 1 mol/L aqueous lithium hydroxide solution (1.2 mL) at room temperature, and this mixture was stirred at same temperature for 5 hours. This mixture was poured into water, this mixture was washed with diethyl ether. To this aqueous layer was added 1 mol/L hydrochloric acid (1.2 mL), and the precipitated solid was collected by filtration, and washed with water and n-hexane. This solid was dried under reduced pressure at 50° C. to give the title compound (0.030 g).

Workup

  1. washthis mixture was washed with diethyl ether
  2. additionTo this aqueous layer was added 1 mol/L hydrochloric acid (1.2 mL)
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water and n-hexane
  5. customThis solid was dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-8dd1a551b5774f7ab386a9a4c94cb4c0
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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