Hydrochloric Acid → 4-{3-Cyano-4-[2-(2-methoxyethoxy)phenyl]pyrrole-1-yl}-2-hydroxy benzoic acid

HRID 1516590Notes

Reaction equation

HRID 1516590 reaction equation
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH2:23][CH2:24][O:25][CH3:26])[C:13]([C:27]#[N:28])=[CH:12]2)=[CH:7][C:6]=1[OH:29])C.C(O)C.[OH-].[Li+].Cl>O.O1CCCC1>[C:27]([C:13]1[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:15][N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:30])=[O:3])=[C:6]([OH:29])[CH:7]=2)[CH:12]=1)#[N:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 685064744-{3-Cyano-4-[2-(2-methoxyethoxy)phenyl]pyrrole-1-yl}-2-hydroxy benzoic acid ethyl ester

Product 1

HCID 250521924-{3-Cyano-4-[2-(2-methoxyethoxy)phenyl]pyrrole-1-yl}-2-hydroxy benzoic acidYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{3-cyano-4-[2-(2-methoxyethoxy)phenyl]pyrrole-1-yl}-2-hydroxy benzoic acid ethyl ester (0.072 g) in a mixed solvent of ethanol (9 mL) and tetrahydrofuran (3 mL) was added 1 mol/mL aqueous lithium hydroxide solution (2.7 mL), and this mixture was stirred at room temperature for 48 hours. This reaction mixture was poured into 1 mol/L hydrochloric acid (2.7 mL), and to this mixture was added water (30 mL). The precipitated solid was collected by filtration. This obtained solid was washed with water, dried under reduced pressure at 50° C. to give the title compound (0.051 g).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washThis obtained solid was washed with water
  3. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-726e7d9b50aa4534ad22eb44ff50eef5
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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